{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T21:12:55Z","timestamp":1787001175492,"version":"build-2736575974"},"reference-count":46,"publisher":"American Chemical Society (ACS)","issue":"21","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Org. Chem."],"published-print":{"date-parts":[[2000,10,1]]},"DOI":"10.1021\/jo991924b","type":"journal-article","created":{"date-parts":[[2002,7,26]],"date-time":"2002-07-26T02:02:09Z","timestamp":1027648929000},"page":"6837-6840","source":"Crossref","is-referenced-by-count":23,"title":["Honulactones:\u2009 New Bishomoscalarane Sesterterpenes from the Indonesian Sponge\n Strepsichordaia aliena<\/i>"],"prefix":"10.1021","volume":"65","author":[{"given":"Jorge I.","family":"Jim\u00e9nez","sequence":"first","affiliation":[{"name":"Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii 96822-2275, Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853-1301, and Marine Ecology and Aquaculture Group, National Institute of Water and Atmospheric Research (NIWA), Taihoro Nukurangi, Private Bag 109-695 Newmarket, Auckland, New Zealand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wesley Y.","family":"Yoshida","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii 96822-2275, Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853-1301, and Marine Ecology and Aquaculture Group, National Institute of Water and Atmospheric Research (NIWA), Taihoro Nukurangi, Private Bag 109-695 Newmarket, Auckland, New Zealand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paul J.","family":"Scheuer","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii 96822-2275, Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853-1301, and Marine Ecology and Aquaculture Group, National Institute of Water and Atmospheric Research (NIWA), Taihoro Nukurangi, Private Bag 109-695 Newmarket, Auckland, New Zealand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Emil","family":"Lobkovsky","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii 96822-2275, Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853-1301, and Marine Ecology and Aquaculture Group, National Institute of Water and Atmospheric Research (NIWA), Taihoro Nukurangi, Private Bag 109-695 Newmarket, Auckland, New Zealand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jon","family":"Clardy","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii 96822-2275, Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853-1301, and Marine Ecology and Aquaculture Group, National Institute of Water and Atmospheric Research (NIWA), Taihoro Nukurangi, Private Bag 109-695 Newmarket, Auckland, New Zealand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michelle","family":"Kelly","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii 96822-2275, Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853-1301, and Marine Ecology and Aquaculture Group, National Institute of Water and Atmospheric Research (NIWA), Taihoro Nukurangi, Private Bag 109-695 Newmarket, Auckland, New Zealand"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2000,9,28]]},"reference":[{"key":"jo991924bb00001\/jo991924bb00001_1","doi-asserted-by":"crossref","first-page":"377","DOI":"10.1021\/np980389s","volume":"62","author":"Jahn T.","year":"1999","journal-title":"J. Nat. Prod."},{"key":"jo991924bb00002\/jo991924bb00002_1","first-page":"154","volume":"62","author":"Sera Y.","year":"1999","journal-title":"J. Nat. Prod."},{"key":"jo991924bb00003\/jo991924bb00003_1","doi-asserted-by":"crossref","first-page":"1485","DOI":"10.1021\/jo961975y","volume":"62","author":"Rueda A.","year":"1997","journal-title":"J. Org. Chem."},{"key":"jo991924bb00004\/jo991924bb00004_1","doi-asserted-by":"crossref","first-page":"6190","DOI":"10.1016\/S0040-4020(98)00311-1","volume":"54","author":"De Rosa S.","year":"1998","journal-title":"Tetrahedron"},{"key":"jo991924bb00005\/jo991924bb00005_1","doi-asserted-by":"crossref","first-page":"561","DOI":"10.1021\/np960147x","volume":"60","author":"Jaspars M.","year":"1997","journal-title":"J. Nat. Prod."},{"key":"jo991924bb00006\/jo991924bb00006_1","doi-asserted-by":"crossref","first-page":"1626","DOI":"10.1016\/0006-2952(91)90432-5","volume":"42","author":"de Carvalho M. S.","year":"1991","journal-title":"Biochem. Pharm."},{"key":"jo991924bb00006\/jo991924bb00006_2","doi-asserted-by":"crossref","first-page":"2086","DOI":"10.1016\/0006-2952(87)90134-1","volume":"36","author":"Glaser K. B.","year":"1987","journal-title":"Biochem. Pharm."},{"key":"jo991924bb00006\/jo991924bb00006_3","first-page":"1717","volume":"55","author":"Potts B. C. M.","year":"1992","journal-title":"J. Nat. Prod."},{"key":"jo991924bb00007\/jo991924bb00007_1","first-page":"111","volume":"37","author":"Yasuda F.","year":"1981","journal-title":"Experientia"},{"key":"jo991924bb00007\/jo991924bb00007_2","doi-asserted-by":"crossref","first-page":"1240","DOI":"10.1021\/np50087a009","volume":"55","author":"Bowden B. F.","year":"1992","journal-title":"J. Nat. Prod."},{"key":"jo991924bb00007\/jo991924bb00007_3","first-page":"517","volume":"59","author":"Ryu G.","year":"1996","journal-title":"J. Nat. Prod."},{"key":"jo991924bb00007\/jo991924bb00007_4","first-page":"1613","volume":"55","author":"Fu X.","year":"1992","journal-title":"J. Nat. Prod."},{"key":"jo991924bb00007\/jo991924bb00007_5","first-page":"16","volume":"61","author":"Pettit G. R.","year":"1998","journal-title":"J. Nat. Prod."},{"key":"jo991924bb00008\/jo991924bb00008_1","doi-asserted-by":"crossref","first-page":"4412","DOI":"10.1016\/S0040-4020(01)87279-3","volume":"42","author":"Terem B.","year":"1986","journal-title":"J. Tetrahedron"},{"key":"jo991924bb00008\/jo991924bb00008_2","doi-asserted-by":"crossref","first-page":"4979","DOI":"10.1021\/jo01312a032","volume":"45","author":"Walker R. P.","year":"1980","journal-title":"J. Org. Chem."},{"key":"jo991924bb00009\/jo991924bb00009_1","first-page":"59","volume":"35","author":"Kazlauskas R.","year":"1982","journal-title":"Aust. J. Chem."},{"key":"jo991924bb00010\/jo991924bb00010_1","first-page":"4614","volume":"41","author":"Braekman J. C.","year":"1985","journal-title":"Tetrahedron"},{"key":"jo991924bb00010\/jo991924bb00010_2","doi-asserted-by":"crossref","first-page":"445","DOI":"10.1016\/S0040-4020(01)87444-5","volume":"42","author":"Braekman J. C.","year":"1986","journal-title":"Tetrahedron"},{"key":"jo991924bb00011\/jo991924bb00011_1","first-page":"865","volume":"55","author":"Alvi K. A.","year":"1992","journal-title":"J. Nat. Prod."},{"key":"jo991924bb00012\/jo991924bb00012_1","first-page":"59","volume":"35","author":"Kazlauskas R.","year":"1982","journal-title":"Aust. J. Chem."},{"key":"jo991924bb00013\/jo991924bb00013_1","volume-title":"which reflects on the collection site at Turtle Bay, eastern Indonesia. Isolation procedure:\u2009 The freeze-dried sponge (81.0 g) was extracted in DCM:IPA (1:1","author":"Honu"},{"key":"jo991924bb00014\/jo991924bb00014_1","volume-title":"eastern Indonesia, at a depth of 23 m","author":"The","year":"1996"},{"key":"jo991924bb00015\/jo991924bb00015_1","first-page":"159","volume":"155","author":"Croft K. D.","year":"1983","journal-title":"J. Chem. Soc., Perkin Trans. 1"},{"key":"jo991924bb00016\/jo991924bb00016_1","unstructured":"Honulactone A (\n 1\n ):\u2009 Colorless crystalline solid, 7.1 mg (0.0088% based on dry weight); [\u03b1]\n D\n = +73.2\u00b0 (\n c\n 0.71, CH\n 2\n Cl\n 2\n ). HRFABMS\n m\n \/\n z\n 499.3431 [M + H]\n +\n (C\n 31\n H\n 47\n O\n 5\n , \u0394 \u22121.5 ppm). IR (thin film) \u03c5\n max\n 3448, 2930, 1742, 1671, 1383, 1324, 1288, 1176, 1064 cm\n -\n 1\n .\n 1\n H NMR (400 MHz, CDCl\n 3\n ) \u03b4 1.70 (dt,\n J\n = 3, 13 Hz, H-1\n eq\n ), 0.71 (m, H-1\n ax\n ), 1.44 (m, H\n 2\n -2), 1.5 (m, H-3\n eq\n ), 1.23 (m, H-3\n ax\n ), 1.37 (m, H-5\n ax\n ), 1.05 (m, H\n 2\n -6), 1.77 (dt,\n J\n = 3, 12 Hz, H-7\n eq\n ), 0.97 (m, H-7\n ax\n ), 1.19 (dd,\n J\n = 2, 14 Hz, H-9\n ax\n ), 2.09 (dt,\n J\n = 3, 15 Hz, H-11\n eq\n ), 1.7 (ddd,\n J\n = 2, 15, 15 Hz, H-11\n ax\n ), 5.61 (br t,\n J\n = 2.6 Hz, H-12\n eq\n ), 1.52 (m, H-14\n ax\n ), 1.91 (dd,\n J\n = 6, 13 Hz, H-15\n eq\n ), 1.54 (m, H-15\n ax\n ), 2.37 (m, H-16\n eq\n ), 2.21 (m, H-16\n ax\n ), 0.58 (dd,\n J\n = 4.5, 8.7 Hz, H-19\n \n cis\n \n ), \u22120.49 (dd,\n J\n = 4.5, 5.6 Hz, H-19\n \n trans\n \n ), 0.7 (ddq;\n J\n = 4, 6, 8.4 Hz; H-20), 0.88 (s, H\n 3\n -21), 0.79 (s, H\n 3\n -22), 1.17 (s, H\n 3\n -23), 4.78 (q,\n J\n = 6.6 Hz, H-24), 1.36 (d,\n J\n = 6.8 Hz, H\n 3\n -26), 1.08 (d,\n J\n = 6.4 Hz, H\n 3\n -27), 2.37 (m, H-2\u2018a), 2.31 (m, H-2\u2018b), 4.10 (m, H-3\u2018), 3.06 (d,\n J\n = 3.1 Hz, HO-3\u2018), and 1.18 (d,\n J\n = 6.9 Hz, H\n 3\n -4\u2018).\n 13\n C NMR (100 MHz, CDCl\n 3\n ) \u03b4 39.7 (C-1), 21.1 (C-2), 33.0 (C-3), 22.6 (C-4), 50.2 (C-5), 17.5 (C-6), 40.0 (C-7), 37.8 (C-8), 51.4 (C-9), 37.2 (C-10), 21.1 (C-11), 74.5 (C-12), 38.4 (C-13), 51.2 (C-14), 16.8 (C-15), 24.0 (C-16), 164.1 (C-17), 132.7 (C-18), 13.6 (C-19), 13.4 (C-20), 16.8 (C-21), 13.9 (C-22), 21.4 (C-23), 77.9 (C-24), 171.3 (C-25), 18.6 (C-26), 13.1 (C-27), 171.5 (C-1\u2018), 43.4 (C-2\u2018), 64.2 (C-3\u2018), and 22.3 (C-4\u2018)."},{"key":"jo991924bb00017\/jo991924bb00017_1","first-page":"269","volume":"48","author":"Crews P.","year":"1985","journal-title":"Fortschr. Chem. Org. Naturst."},{"key":"jo991924bb00018\/jo991924bb00018_1","first-page":"10","volume":"16","author":"Seo S.","year":"1975","journal-title":"Tetrahedron Lett."},{"key":"jo991924bb00018\/jo991924bb00018_2","first-page":"229","volume":"36","author":"Wehrli F.","year":"1979","journal-title":"Fortschr. Chem. Org. Naturst."},{"key":"jo991924bb00019\/jo991924bb00019_1","unstructured":"Honulactone B (\n 2\n ):\u2009 Colorless crystalline solid, 6.0 mg (0.0074% based on dry weight); [\u03b1]\n D\n = +77\u00b0 (\n c\n 0.6, CH\n 2\n Cl\n 2\n ). HRFABMS\n m\n \/\n z\n 499.3417 [M + H]\n +\n (C\n 31\n H\n 47\n O\n 5\n , \u0394 1.3 ppm). IR (thin film) \u03c5\n max\n 3448, 2962, 2930, 2869, 1742, 1671, 1458, 1384, 1268, 1175, 1021 cm\n -\n 1\n .\n 1\n H NMR (400 MHz, CDCl\n 3\n ) Proton chemical shifts for\n 2\n are within \u00b10.03 ppm of the values for\n 1\n .\n 13\n C NMR (100 MHz, CDCl\n 3\n ) Carbon chemical shifts for\n 2\n are identical to\n 1\n except for \u03b4 51.5 (C-14), 16.6 (C-15), 24.3 (C-16), and 78.1 (C-24)."},{"key":"jo991924bb00020\/jo991924bb00020_1","unstructured":"Honulactone E (\n 5\n ):\u2009 Colorless crystalline solid, 4.5 mg (0.0056% based on dry weight); [\u03b1]\n D\n = +105.2\u00b0 (\n c\n 1.5, CH\n 2\n Cl\n 2\n ). HRMS (DCI)\n m\n \/\n z\n 530.383397 [M + NH\n 4\n ]\n +\n (C\n 32\n H\n 52\n NO\n 5\n , \u0394 2.2 ppm). IR (thin film) \u03c5\n max\n 3500, 2900, 1740, 1680 cm\n -\n 1\n .\n 1\n H NMR (500 MHz, CDCl\n 3\n ) \u03b4 1.70 (m, H-1\n eq\n ), 0.71 (m, H-1\n ax\n ), 1.45 (m, H\n 2\n -2), 1.53 (m, H-3\n eq\n ), 1.22 (m, H-3\n ax\n ), 1.37 (m, H-5\n ax\n ), 1.03 (m, H\n 2\n -6), 1.76 (dt,\n J\n = 3, 12 Hz, H-7\n eq\n ), 0.97 (m, H-7\n ax\n ), 1.19 (m, H-9\n ax\n ), 2.10 (dt,\n J\n = 3, 15 Hz, H-11\n eq\n ), 1.71 (m, H-11\n ax\n ), 5.60 (br t,\n J\n = 2.7 Hz, H-12\n eq\n ), 1.52 (m, H-14\n ax\n ), 1.90 (dd,\n J\n = 7, 13 Hz, H-15\n eq\n ), 1.55 (m, H-15\n ax\n ), 2.37 (m, H-16\n eq\n ), 2.22 (m, H-16\n ax\n ), 0.57 (dd,\n J\n = 4.2, 8.7 Hz, H-19\n \n cis\n \n ), \u22120.49 (t,\n J\n = 5.2 Hz, H-19\n \n trans\n \n ), 0.69 (m, H-20), 0.87 (s, H\n 3\n -21), 0.78 (s, H\n 3\n -22), 1.17 (s, H\n 3\n -23), 4.77 (q,\n J\n = 6.8 Hz, H-24), 1.36 (d,\n J\n = 6.8 Hz, H\n 3\n -26), 1.07 (d,\n J\n = 6.3 Hz, H\n 3\n -27), 2.38 (m, H-2\u2018a), 2.30 (m, H-2\u2018b), 3.82 (m, H-3\u2018), 2.99 (s, HO-3\u2018), 1.48 (m, H\n 2\n -4\u2018), and 0.93 (t,\n J\n = 7.5 Hz, H\n 3\n -5\u2018).\n 13\n C NMR (125 MHz, CDCl\n 3\n ) \u03b4 39.6 (C-1), 21.1 (C-2), 33.0 (C-3), 22.6 (C-4), 50.2 (C-5), 17.4 (C-6), 40.0 (C-7), 37.8 (C-8), 51.3 (C-9), 37.2 (C-10), 21.0 (C-11), 74.5 (C-12), 38.4 (C-13), 51.1 (C-14), 16.8 (C-15), 24.0 (C-16), 164.1 (C-17), 132.7 (C-18), 13.5 (C-19), 13.3 (C-20), 16.8 (C-21), 13.7 (C-22), 21.4 (C-23), 77.9 (C-24), 171.3 (C-25), 18.6 (C-26), 13.1 (C-27), 171.1 (C-1\u2018), 41.5 (C-2\u2018), 69.4 (C-3\u2018), 29.3 (C-4\u2018), and 10.0 (C-5\u2018)."},{"key":"jo991924bb00021\/jo991924bb00021_1","unstructured":"Honulactone F (\n 6\n ):\u2009 Colorless crystalline solid, 3.4 mg (0.0042% based on dry weight); [\u03b1]\n D\n = +81.5\u00b0 (\n c\n 1.1, CH\n 2\n Cl\n 2\n ). HRMS (DCI)\n m\n \/\n z\n 530.382715 [M + NH\n 4\n ]\n +\n (C\n 32\n H\n 52\n NO\n 5\n , \u0394 3.5 ppm). IR (thin film) \u03c5\n max\n 3450, 2890, 1730, 1650 cm\n -\n 1\n .\n 1\n H NMR (500 MHz, CDCl\n 3\n ) Proton chemical shifts for\n 6\n are within \u00b10.02 ppm of the values for\n 5\n .\n 13\n C NMR (125 MHz, CDCl\n 3\n ) Carbon chemical shift values for\n 6\n are identical to\n 5\n except for \u03b4 51.4 (C-14), 16.5 (C-15), 24.3 (C-16), and 78.1 (C-24)."},{"key":"jo991924bb00022\/jo991924bb00022_1","unstructured":"Honulactone G (\n 7\n ):\u2009 Colorless crystalline solid, 1.7 mg (0.0021% based on dry weight); [\u03b1]\n D\n = +85.7\u00b0 (\n c\n 0.85, CH\n 2\n Cl\n 2\n ). HRMS (DCI)\n m\n \/\n z\n 532.366487 [M + NH\n 4\n ]\n +\n (C\n 31\n H\n 50\n NO\n 6\n , \u0394 \u22125.0 ppm). IR (thin film) \u03c5\n max\n 3500, 3400, 2990, 1735, 1660 cm\n -\n 1\n .\n 1\n H NMR (500 MHz, CDCl\n 3\n ) \u03b4 1.70 (m, H-1\n eq\n ), 0.70 (m, H-1\n ax\n ), 1.50 (m, H-2\n eq\n ), 1.45 (m, H-2\n ax\n ), 1.50 (m, H-3\n eq\n ), 1.25 (m, H-3\n ax\n ), 1.41 (m, H-5\n ax\n ), 1.05 (m, H\n 2\n -6), 1.70 (m, H-7\n eq\n ), 1.05 (m, H-7\n ax\n ), 1.27 (m, H-9\n ax\n ), 2.11 (dt,\n J\n = 3, 15 Hz, H-11\n eq\n ), 1.70 (m, H-11\n ax\n ), 5.62 (br t,\n J\n = 2.7 Hz, H-12\n eq\n ), 1.80 (m, H-14\n ax\n ), 1.85 (m, H\n 2\n -15), 4.44 (s, H-16\n eq\n ), 0.58 (dd,\n J\n = 4.2, 8.7 Hz, H-19\n \n cis\n \n ), \u22120.49 (t,\n J\n = 5.2 Hz, H-19\n \n trans\n \n ), 0.68 (m, H-20), 0.86 (s, H\n 3\n -21), 0.79 (s, H\n 3\n -22), 1.14 (s, H\n 3\n -23), 5.08 (q,\n J\n = 6.8 Hz, H-24), 1.41 (d,\n J\n = 6.8 Hz, H\n 3\n -26), 1.08 (d,\n J\n = 6.3 Hz, H\n 3\n -27), 2.34 (m, H\n 2\n -2\u2018), 4.10 (m, H-3\u2018), 3.03 (s, HO-3\u2018), and 1.20 (d,\n J\n = 6.9 Hz, H\n 3\n -4\u2018).\n 13\n C NMR (125 MHz, CDCl\n 3\n ) \u03b4 39.7 (C-1), 21.2 (C-2), 33.0 (C-3), 22.6 (C-4), 50.2 (C-5), 17.4 (C-6), 39.9 (C-7), 36.7 (C-8), 51.4 (C-9), 37.8 (C-10), 21.1 (C-11), 74.2 (C-12), 39.0 (C-13), 45.9 (C-14), 27.7 (C-15), 61.5 (C-16), 162.0 (C-17), 135.5 (C-18), 13.6 (C-19), 13.4 (C-20), 16.8 (C-21), 13.9 (C-22), 19.7 (C-23), 76.6 (C-24), 170.8 (C-25), 18.0 (C-26), 13.1 (C-27), 171.5 (C-1\u2018), 43.4 (C-2\u2018), 64.3 (C-3\u2018), and 22.4 (C-4\u2018)."},{"key":"jo991924bb00023\/jo991924bb00023_1","unstructured":"Honulactone H (\n 8\n ):\u2009 Colorless crystalline solid, 1.5 mg (0.0019% based on dry weight); [\u03b1]\n D\n = +78.3\u00b0 (\n c\n 0.75, CH\n 2\n Cl\n 2\n ). HRMS (DCI)\n m\n \/\n z\n 532.364078 [M + NH\n 4\n ]\n +\n (C\n 31\n H\n 50\n NO\n 6\n , \u0394 \u22120.5 ppm). IR (thin film) \u03c5\n max\n 3505, 3200, 2900, 1745, 1670 cm\n -\n 1\n .\n 1\n H NMR (500 MHz, CDCl\n 3\n ) Proton chemical shifts for\n 8\n are within \u00b10.03 ppm of the values for\n 7\n except for \u03b4 4.90 (q,\n J\n = 6.8 Hz, H-24), 1.52 (d,\n J\n = 6.8 Hz, H\n 3\n -26), 2.37 (m, H-2\u2018a), and 2.36 (m, H-2\u2018b).\n 13\n C NMR (125 MHz, CDCl\n 3\n ) Carbon chemical shift values for\n 8\n are identical to\n 7\n except for \u03b4 62.9 (C-16), 160.8 (C-17), 78.9 (C-24), and 19.8 (C-26)."},{"key":"jo991924bb00024\/jo991924bb00024_1","unstructured":"Suitable crystals of honulactone B (\n 2\n ) for X-ray analysis were obtained from isooctane\/dichloromethane. The compound crystallized in the tetragonal space group\n P\n 4\n 3\n 2\n 1\n 2 with a unit cell having the dimensions\n a\n = 29.924 (1) \u00c2,\n b\n = 29.924 (1) \u00c2,\n c\n = 7.3309 (4) \u00c2, and a calculated density of 1.009 g cm\n -\n 3\n . A colorless crystal (0.40 \u00d7 0.10 \u00d7 0.10 mm\n 3\n ) mounted on a thin glass rod was used for the data collection. A total of 1321 frames of data were taken on a BRUKER SMART CCD Area Detector System equipped with a 3 kW sealed tube (Mo K\u03b1) X-ray generator. A narrow-frame method was used with a scan widths of 0.3\u00b0 in \u03c9 and an exposure time of 30 s\/frame. Frames were integrated to yield a total of 18626 reflections of which 2577 were independent (\n R\n int\n = 7.31%), and 2343 were above 4\u03c3(\n F\n ). The structure was solved by direct methods and refined by full-matrix least squares on\n F\n \u2009\n 2\n using anisotropic displacement parameters for all non-hydrogen atoms. At final convergence,\n R\n 1\n = 8.63% and GOF = 1.040 for 340 parameters. Additional X-ray data are available in the Supporting Information and the Cambridge Crystallographic Data file."},{"key":"jo991924bb00025\/jo991924bb00025_1","unstructured":"Honulactone C (\n 3\n ):\u2009 Colorless crystalline solid, 7.6 mg (0.0094% based on dry weight); [\u03b1]\n D\n = +71.2\u00b0 (\n c\n 0.57, CH\n 2\n Cl\n 2\n ). HRFABMS\n m\n \/\n z\n 559.3615 [M + H]\n +\n (C\n 33\n H\n 51\n O\n 7\n , \u0394 3.5 ppm). IR (thin film) \u03c5\n max\n 3498, 2969, 1738, 1672, 1372, 1033 cm\n -\n 1\n .\n 1\n H NMR (500 MHz, CDCl\n 3\n ) \u03b4 1.64 (m, H-1\n eq\n ), 0.62 (ddd,\n J\n = 4, 13, 13 Hz, H-1\n ax\n ), 1.43 (m, H-2\n eq\n ), 1.34 (m, H-2\n ax\n ), 1.63 (m, H-3\n eq\n ), 0.99 (ddd,\n J\n = 4, 14, 14 Hz, H-3\n ax\n ), 0.94 (m, H-5\n ax\n ), 1.74 (m, H-6\n eq\n ), 1.42 (m, H-6\n ax\n ), 1.81 (dt,\n J\n = 3, 13 Hz, H-7\n eq\n ), 0.90 (ddd,\n J\n = 3, 13, 13 Hz, H-7\n ax\n ), 1.14 (dd,\n J\n = 3, 13 Hz, H-9\n ax\n ), 2.01 (dt,\n J\n = 3, 13 Hz, H-11\n eq\n ), 1.68 (m, H-11\n ax\n ), 5.58 (br t,\n J\n = 2.7 Hz, H-12\n eq\n ), 1.48 (d,\n J\n = 13 Hz, H-14\n ax\n ), 1.88 (dt,\n J\n = 3, 13 Hz, H-15\n eq\n ), 1.53 (m, H-15\n ax\n ), 2.35 (m, H-16\n eq\n ), 2.19 (m, H-16\n ax\n ), 0.95 (s, H\n 3\n -19), 5.34 (q,\n J\n = 6.3 Hz, H-20), 0.85 (s, H\n 3\n -21), 0.85 (s, H\n 3\n -22), 1.16 (s, H\n 3\n -23), 4.77 (q,\n J\n = 6.6 Hz, H-24), 1.34 (d,\n J\n = 6.6 Hz, H\n 3\n -26), 1.07 (d,\n J\n = 6.3 Hz, H\n 3\n -27), 2.02 (s, C\n H\n 3\n CO), 2.33 (m, H-2\u2018a), 2.31 (m, H-2\u2018b), 4.07 (m, H-3\u2018), 3.07 (s, HO-3\u2018), and 1.17 (d,\n J\n = 6.6 Hz, H\n 3\n -4\u2018).\n 13\n C NMR (125 MHz, CDCl\n 3\n ) \u03b4 40.3 (C-1), 17.7 (C-2), 38.9 (C-3), 39.2 (C-4), 58.8 (C-5), 19.9 (C-6), 42.3 (C-7), 37.5 (C-8), 53.7 (C-9), 37.1 (C-10), 21.0 (C-11), 74.4 (C-12), 38.3 (C-13), 51.0 (C-14), 16.7 (C-15), 24.0 (C-16), 164.3 (C-17), 132.6 (C-18), 23.1 (C-19), 73.1 (C-20), 16.6 (C-21), 16.4 (C-22), 21.4 (C-23), 77.9 (C-24), 171.3 (C-25), 18.6 (C-26), 15.7 (C-27), 170.3 (CH\n 3\n C\n O), 21.8 (\n C\n H\n 3\n CO), 171.4 (C-1\u2018), 43.3 (C-2\u2018), 64.2 (C-3\u2018), and 22.2 (C-4\u2018)."},{"key":"jo991924bb00026\/jo991924bb00026_1","doi-asserted-by":"crossref","first-page":"427","DOI":"10.1021\/np50074a012","volume":"54","author":"Zeng L.","year":"1991","journal-title":"J. Nat. Prod."},{"key":"jo991924bb00026\/jo991924bb00026_2","first-page":"556","volume":"31","author":"Kikuchi H.","year":"1983","journal-title":"Chem. Pharm. Bull."},{"key":"jo991924bb00026\/jo991924bb00026_3","first-page":"2082","volume":"37","author":"Kitagawa I.","year":"1989","journal-title":"Chem. Pharm. Bull."},{"key":"jo991924bb00026\/jo991924bb00026_4","doi-asserted-by":"crossref","first-page":"999","DOI":"10.1071\/CH9910995","volume":"44","author":"Barron P. E.","year":"1991","journal-title":"Aust. J. Chem."},{"key":"jo991924bb00026\/jo991924bb00026_5","doi-asserted-by":"crossref","first-page":"755","DOI":"10.1071\/CH9890751","volume":"42","author":"Quinn R. J.","year":"1989","journal-title":"Aust. J. Chem."},{"key":"jo991924bb00027\/jo991924bb00027_1","unstructured":"Honulactone D (\n 4\n ):\u2009 Colorless crystalline solid, 4.5 mg (0.0056% based on dry weight); [\u03b1]\n D\n = +62.0\u00b0 (\n c\n 0.25, CH\n 2\n Cl\n 2\n ). HRFABMS\n m\n \/\n z\n 559.3618 [M + H]\n +\n (C\n 33\n H\n 51\n O\n 7\n , \u0394 3.0 ppm). IR (thin film) \u03c5\n max\n 3498, 2969, 1738, 1732, 1672, 1254, 1033 cm\n -\n 1\n .\n 1\n H NMR (500 MHz, CDCl\n 3\n ) Proton chemical shifts for\n 4\n are within \u00b10.05 ppm of the values for\n 3\n except for \u03b4 2.33 (d,\n J\n = 6 Hz, H\n 2\n -2\u2018).\n 13\n C NMR (125 MHz, CDCl\n 3\n ) Carbon chemical shift values for\n 4\n are identical to\n 3\n except for \u03b4 78.1 (C-24)."},{"key":"jo991924bb00028\/jo991924bb00028_1","unstructured":"Honulactone I (\n 9\n ):\u2009 Colorless crystalline solid, 2.4 mg (0.003% based on dry weight); [\u03b1]\n D\n = +83.4\u00b0 (\n c\n 0.96, CH\n 2\n Cl\n 2\n ). HRMS (FAB)\n m\n \/\n z\n 573.37913 [M + H]\n +\n (C\n 34\n H\n 53\n O\n 7\n , \u0394 \u22124.5 ppm). IR (thin film) \u03c5\n max\n 3490, 2970, 1725, 1660, 1360, 1025 cm\n -\n 1\n .\n 1\n H NMR (500 MHz, CDCl\n 3\n ) \u03b4 1.72 (m, H-1\n eq\n ), 0.64 (ddd,\n J\n = 4, 13, 13 Hz, H-1\n ax\n ), 1.45 (m, H-2\n eq\n ), 1.35 (m, H-2\n ax\n ), 1.66 (m, H-3\n eq\n ), 1.00 (ddd,\n J\n = 4, 14, 14 Hz, H-3\n ax\n ), 0.96 (m, H-5\n ax\n ), 1.75 (m, H-6\n eq\n ), 1.43 (m, H-6\n ax\n ), 1.81 (dt,\n J\n = 3, 13 Hz, H-7\n eq\n ), 0.91 (m, H-7\n ax\n ), 1.14 (dd,\n J\n = 3, 13 Hz, H-9\n ax\n ), 2.04 (dt,\n J\n = 3, 13 Hz, H-11\n eq\n ), 1.69 (m, H-11\n ax\n ), 5.60 (br t,\n J\n = 2.9 Hz, H-12\n eq\n ), 1.50 (m, H-14\n ax\n ), 1.89 (dt,\n J\n = 7, 13 Hz, H-15\n eq\n ), 1.55 (m, H-15\n ax\n ), 2.36 (d,\n J\n = 15 Hz, H-16\n eq\n ), 2.19 (m, H-16\n ax\n ), 0.96 (s, H\n 3\n -19), 5.35 (q,\n J\n = 6.9 Hz, H-20), 0.86 (s, H\n 3\n -21), 0.86 (s, H\n 3\n -22), 1.17 (s, H\n 3\n -23), 4.76 (q,\n J\n = 6.9 Hz, H-24), 1.35 (d,\n J\n = 7.0 Hz, H\n 3\n -26), 1.08 (d,\n J\n = 7.0 Hz, H\n 3\n -27), 2.03 (s, C\n H\n 3\n CO), 2.37 (dd,\n J\n = 3, 16 Hz, H-2\u2018a), 2.29 (dd,\n J\n = 9, 16 Hz, H-2\u2018b), 3.82 (m, H-3\u2018), 2.95 (s, HO-3\u2018), 1.47 (m, H\n 2\n -4\u2018), and 0.93 (t,\n J\n = 7.6 Hz, H\n 3\n -5\u2018).\n 13\n C NMR (125 MHz, CDCl\n 3\n ) \u03b4 40.3 (C-1), 17.8 (C-2), 39.0 (C-3), 39.2 (C-4), 58.9 (C-5), 20.0 (C-6), 42.4 (C-7), 37.5 (C-8), 53.8 (C-9), 37.1 (C-10), 21.0 (C-11), 74.5 (C-12), 38.3 (C-13), 51.0 (C-14), 16.8 (C-15), 24.0 (C-16), 164.0 (C-17), 132.7 (C-18), 23.2 (C-19), 73.1 (C-20), 16.6 (C-21), 16.5 (C-22), 21.4 (C-23), 77.8 (C-24), 171.2 (C-25), 18.6 (C-26), 15.8 (C-27), 170.3 (CH\n 3\n C\n O), 21.8 (\n C\n H\n 3\n CO), 171.6 (C-1\u2018), 41.5 (C-2\u2018), 69.4 (C-3\u2018), 29.3 (C-4\u2018), and 10.0 (C-5\u2018)."},{"key":"jo991924bb00029\/jo991924bb00029_1","unstructured":"Honulactone J (\n 10\n ):\u2009 Colorless crystalline solid, 2.6 mg (0.0032% based on dry weight); [\u03b1]\n D\n = +80.7\u00b0 (\n c\n 0.67, CH\n 2\n Cl\n 2\n ). HRMS (DCI)\n m\n \/\n z\n 590.403408 [M + NH\n 4\n ]\n +\n (C\n 34\n H\n 56\n NO\n 7\n , \u0394 3.8 ppm). IR (thin film) \u03c5\n max\n 3500, 2990, 1750, 1650 cm\n -\n 1\n .\n 1\n H NMR (500 MHz, CDCl\n 3\n ) Proton chemical shifts for\n 10\n are within \u00b10.05 ppm of the values for\n 9\n except for \u03b4 2.36 (m, H-16\n eq\n ), and 2.25 (m, H-16\n ax\n ).\n 13\n C NMR (125 MHz, CDCl\n 3\n ) Carbon chemical shifts for\n 10\n are identical to\n 9\n except for \u03b4 78.1 (C-24)."},{"key":"jo991924bb00030\/jo991924bb00030_1","unstructured":"Honulactone K (\n 11\n ):\u2009 Colorless crystalline solid, 2.3 mg (0.0028% based on dry weight); [\u03b1]\n D\n = +90.1\u00b0 (\n c\n 0.77, CH\n 2\n Cl\n 2\n ). HRMS (DCI)\n m\n \/\n z\n 590.402819 [M + NH\n 4\n ]\n +\n (C\n 34\n H\n 56\n NO\n 7\n , \u0394 4.8 ppm). IR (thin film) \u03c5\n max\n 3560, 3020, 2900, 1760, 1670 cm\n -\n 1\n .\n 1\n H NMR (500 MHz, CDCl\n 3\n ) \u03b4 1.66 (m, H-1\n eq\n ), 0.63 (ddd,\n J\n = 4, 13, 13 Hz, H-1\n ax\n ), 1.43 (m, H-2\n eq\n ), 1.33 (m, H-2\n ax\n ), 1.64 (m, H-3\n eq\n ), 1.00 (ddd,\n J\n = 4, 14, 14 Hz, H-3\n ax\n ), 0.95 (m, H-5\n ax\n ), 1.70 (m, H-6\n eq\n ), 1.40 (m, H-6\n ax\n ), 1.80 (dt,\n J\n = 3, 13 Hz, H-7\n eq\n ), 0.89 (m, H-7\n ax\n ), 1.12 (m, H-9\n ax\n ), 2.02 (dt,\n J\n = 3, 15 Hz, H-11\n eq\n ), 1.55 (m, H-11\n ax\n ), 5.60 (br t,\n J\n = 2.7 Hz, H-12\n eq\n ), 1.49 (m, H-14\n ax\n ), 1.89 (dd,\n J\n = 7, 13 Hz, H-15\n eq\n ), 1.55 (m, H-15\n ax\n ), 2.35 (m, H-16\n eq\n ), 2.19 (m, H-16\n ax\n ), 0.97 (s, H\n 3\n -19), 5.38 (q,\n J\n = 6.3 Hz, H-20), 0.85 (s, H\n 3\n -21), 0.86 (s, H\n 3\n -22), 1.17 (s, H\n 3\n -23), 4.77 (q,\n J\n = 6.8 Hz, H-24), 1.35 (d,\n J\n = 6.8 Hz, H\n 3\n -26), 1.07 (d,\n J\n = 6.3 Hz, H\n 3\n -27), 1.15 (t,\n J\n = 7.7 Hz, C\n H\n 3\n CH\n 2\n CO), 2.30 (m, CH\n 3\n C\n H\n 2\n CO), 2.32 (m, H-2\u2018a), 2.30 (m, H-2\u2018b), 4.10 (m, H-3\u2018), 3.05 (s, HO-3\u2018), and 1.18 (d,\n J\n = 6.3 Hz, H\n 3\n -4\u2018).\n 13\n C NMR (125 MHz, CDCl\n 3\n ) \u03b4 40.3 (C-1), 17.8 (C-2), 39.0 (C-3), 39.3 (C-4), 58.9 (C-5), 20.1 (C-6), 42.3 (C-7), 37.5 (C-8), 53.8 (C-9), 37.1 (C-10), 21.0 (C-11), 74.5 (C-12), 38.3 (C-13), 51.0 (C-14), 16.7 (C-15), 24.0 (C-16), 164.1 (C-17), 132.7 (C-18), 23.2 (C-19), 72.8 (C-20), 16.5 (C-21), 16.6 (C-22), 21.4 (C-23), 77.9 (C-24), 171.3 (C-25), 18.6 (C-26), 15.8 (C-27), 173.5 (CH\n 3\n CH\n 2\n C\n O), 28.5 (CH\n 3\n C\n H\n 2\n CO), 9.2 (\n C\n H\n 3\n CH\n 2\n CO), 171.5 (C-1\u2018), 43.4 (C-2\u2018), 64.2 (C-3\u2018), and 22.2 (C-4\u2018)."},{"key":"jo991924bb00031\/jo991924bb00031_1","unstructured":"Honulactone L (\n 12\n ):\u2009 Colorless crystalline solid, 1.6 mg (0.002% based on dry weight); [\u03b1]\n D\n = +74\u00b0 (\n c\n 0.8, CH\n 2\n Cl\n 2\n ). HRMS (DCI)\n m\n \/\n z\n 590.403456 [M + NH\n 4\n ]\n +\n (C\n 34\n H\n 56\n NO\n 7\n , \u0394 3.8 ppm). IR (thin film) \u03c5\n max\n 3565, 3025, 2910, 1770, 1660 cm\n -\n 1\n .\n 1\n H NMR (500 MHz, CDCl\n 3\n ) Proton chemical shifts for\n 11\n are within \u00b10.05 ppm of the values for\n 10\n except for \u03b4 2.32 (m, H\n 2\n -2\u2018).\n 13\n C NMR (125 MHz, CDCl\n 3\n ) Carbon chemical shift values for\n 11\n are identical to\n 10\n except for \u03b4 78.1 (C-24)."},{"key":"jo991924bb00032\/jo991924bb00032_1","unstructured":"Suitable crystals of honulactone D (\n 4\n ) for X-ray analysis were obtained from isooctane\/dichloromethane. The compound crystallized in the orthorhombic space group\n P\n 2\n 1\n 2\n 1\n 2\n 1\n with a unit cell having the dimensions\n a\n = 7.5059(1) \u00c5,\n b\n = 14.1990(3) \u00c5,\n c\n = 28.7786(10) \u00c5, and a calculated density of 1.21 g cm\n -\n 3\n . A colorless crystal (0.15 \u00d7 0.10 \u00d7 0.10 mm\n 3\n ) mounted on a thin glass rod was used for the data collection. A total of 1321 frames of data were taken on a BRUKER SMART CCD Area Detector System equipped with a 3 kW sealed tube (Mo K\u03b1) X-ray generator. A narrow-frame method was used with a scan widths of 0.3\u00b0 in \u03c9 and an exposure time of 30 s\/frame. Frames were integrated to yield a total of 9611 reflections of which 3530 were independent (\n R\n int\n = 11.08%), and 3295 were above 4\u03c3(\n F\n ). It was impossible to cut a single crystal out of a conglomerate, so the low-resolution data were heavily compromised by reflections from small satellite crystals and discarded. The structure was solved by direct methods and refined by full-matrix least squares on\n F\n \u2009\n 2\n using anisotropic displacement parameters for all non-hydrogen atoms. At final convergence,\n R\n 1\n = 7.73% and GOF = 1.042 for 361 parameters. Additional X-ray data are available in the Supporting Information and the Cambridge Crystallographic Data file."},{"key":"jo991924bb00033\/jo991924bb00033_1","doi-asserted-by":"crossref","first-page":"1677","DOI":"10.1135\/cccc19981671","volume":"63","author":"Pettit G. R.","year":"1998","journal-title":"Coll. Czech. Chem. Commun."}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jo991924b","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,9,23]],"date-time":"2021-09-23T12:01:34Z","timestamp":1632398494000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/jo991924b"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2000,9,28]]},"references-count":46,"journal-issue":{"issue":"21","published-print":{"date-parts":[[2000,10,1]]}},"alternative-id":["10.1021\/jo991924b"],"URL":"https:\/\/doi.org\/10.1021\/jo991924b","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2000,9,28]]}}}