{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,8]],"date-time":"2026-03-08T20:53:15Z","timestamp":1773003195110,"version":"3.50.1"},"reference-count":11,"publisher":"CLOCKSS Archive","issue":"9","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["HETEROCYCLES"],"published-print":{"date-parts":[[2000]]},"DOI":"10.3987\/com-00-8975","type":"journal-article","created":{"date-parts":[[2009,3,3]],"date-time":"2009-03-03T01:38:43Z","timestamp":1236044323000},"page":"1877","source":"Crossref","is-referenced-by-count":23,"title":["The First Total Synthesis of (R)-(-)-Pyridindolol K2 and Its Enantiomer"],"prefix":"10.13030","volume":"53","author":[{"given":"Satoshi","family":"Hibino","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Naoko","family":"Kanekiyo","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tominari","family":"Choshi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Takeshi","family":"Kuwada","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Eiichi","family":"Sugino","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"5187","reference":[{"key":"10.3987\/COM-00-8975-1","doi-asserted-by":"crossref","unstructured":"1. Y.-P. Kim, S. Takamatsu, M. Hayashi, K. Komiyama, and S. Omura, J. Antibiotics, 1997, 50, 189.","DOI":"10.7164\/antibiotics.50.878"},{"key":"10.3987\/COM-00-8975-2","doi-asserted-by":"crossref","unstructured":"2 .T. Aoyagi, M. Kumagai, T. Hazato, M. Hamada, T. Takeuchi, and H. Umezawa, ibid., 1975, 28, 555; M. Kumagai, H. Nagasawa, T. Aoyagi, and H. Umezawa, ibid., 1975, 28, 876; M. Kumagai, T. Aoyagi, and H. Umezawa, ibid., 1976, 29, 696.","DOI":"10.7164\/antibiotics.28.555"},{"key":"10.3987\/COM-00-8975-3","doi-asserted-by":"crossref","unstructured":"3 .L. Hagmann and W. Keller-Sherlein, J. Antibiotics, 1988, 41, 289.","DOI":"10.7164\/antibiotics.41.289"},{"key":"10.3987\/COM-00-8975-4","unstructured":"4. T. Choshi, T. Sada, H. Fujimoto, C. Nagayama, E. Sugino, and S. Hibino, J. Org. Chem., 1997, 62, 2535."},{"key":"10.3987\/COM-00-8975-5","unstructured":"5. All new compounds provided satisfactory spectral and physical data."},{"key":"10.3987\/COM-00-8975-6","unstructured":"6. T. Sakamoto, A. Numata, H. Saitoh, and Y. Kondo, Chem. Pharm. Bull., 1999, 47, 1740."},{"key":"10.3987\/COM-00-8975-7","doi-asserted-by":"crossref","unstructured":"7. T. Sakamoto, A. Numata, K. Hayashi, and Y. Kondo, ibid., 2000, 48, 669.","DOI":"10.1248\/cpb.48.669"},{"key":"10.3987\/COM-00-8975-8","doi-asserted-by":"crossref","unstructured":"8. T. Choshi, T. Kuwada, M. Fukui, Y. Matsuya, E. Sugino, and S. Hibino, Chem. Pharm. Bull., 2000, 48, 108.","DOI":"10.1248\/cpb.48.108"},{"key":"10.3987\/COM-00-8975-9","unstructured":"9. K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L.Kwong, Z.-M. Wang, D. Zu, and X.-L. Zhang, J. Org. Chem., 1992, 57, 2768."},{"key":"10.3987\/COM-00-8975-10","unstructured":"10. (S)-(+)-Pyridindolol K2 (2a): mp 124-125\u00b0C (MeOH-CHCl3); 1H-NMR (300 MHz, MeOH-d4) \u03b4 2.13 (3H, s), 3.97 (2H, br s), 5.20 (1H, br s), 5.32 (2H, s), 7.22 (1H, t, J=7.7 Hz), 7.53 (1H, dd, J=7.0, 1.1 Hz), 7.60 (1H, d, J=8.0 Hz), 8.05 (1H, s), 8.15 (1H, d, J=8.0 Hz); 13C-NMR (75 MHz, MeOH- d4) \u03b4 20.9, 67.0, 68.4, 76.0, 113.0, 114.3, 120.7, 122.0, 122.5, 129.6, 131.6, 134.7, 142.8, 144.1, 145.7, 172.7; MS m\/z: 300 (M+). (R)-(-)-Pyridindolol K2 (2): mp 123-124\u00b0C (MeOH-CHCl3); 1H-NMR (300 MHz, MeOH- d4) \u03b4 2.13 (3H, s), 3.97 (2H, br s), 5.20 (1H, br s), 5.32 (2H, s), 7.22 (1H, t, J=7.0 Hz), 7.54 (1H, dd, J=8.0, 1.1 Hz), 7.60 (1H, d, J=8.0 Hz), 8.05 (1H, s), 8.15 (1H, d, J=8.0 Hz); 13C-NMR (75 MHz, MeOH- d4) \u03b4 20.9, 67.0, 68.4, 76.1, 113.0, 114.3, 120.7, 122.0, 122.5, 129.6, 131.6, 134.7, 142.8, 144.2, 145.7, 172.7; MS m\/z: 300 (M+)."},{"key":"10.3987\/COM-00-8975-11","doi-asserted-by":"crossref","unstructured":"11. H. Yoshioka, Y. Matsuya, T. Choshi, E. Sugino, and S. Hibino, Chem. Pharm. Bull., 1996, 44, 709; T. Choshi, Y. Matsuya, M. Okita, K. Inada, E. Sugino, and S. Hibino, Tetrahedron Lett., 1998, 39, 2341; N. Kuwabara, H. Hayashi, N. Hiramatsu, T. Choshi, E. Sugino, and S. Hibino, Chem. Pharm. Bull., 1999, 47, 1805 and related references cited therein.","DOI":"10.1248\/cpb.44.709"}],"container-title":["HETEROCYCLES"],"original-title":[],"language":"en","deposited":{"date-parts":[[2024,6,24]],"date-time":"2024-06-24T19:48:49Z","timestamp":1719258529000},"score":1,"resource":{"primary":{"URL":"https:\/\/triggered.stanford.clockss.org\/ServeContent?doi=10.3987%2Fcom-00-8975"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2000]]},"references-count":11,"journal-issue":{"issue":"9","published-print":{"date-parts":[[2000]]}},"alternative-id":["COM-00-8975"],"URL":"https:\/\/doi.org\/10.3987\/com-00-8975","relation":{},"ISSN":["0385-5414"],"issn-type":[{"value":"0385-5414","type":"print"}],"subject":[],"published":{"date-parts":[[2000]]}}}