none 10.3987/COM-00-9014 CLOCKSS Archive CLOCKSS Archive 5187 36504730 73640 20090309132624 10.13030 2024-06-24T20:31:02Z 2009-03-09T04:27:29Z 12 HETEROCYCLES HETEROCYCLES 0385-5414 HTCYAM 2001 55 1 Synthesis of Apicidin Takeshi Kitahara Wataru Kuriyama 2001 1 COM-00-9014 10.3987/COM-00-9014 20090309132624 https://triggered.stanford.clockss.org/ServeContent?doi=10.3987%2Fcom-00-9014 https://triggered.edinburgh.clockss.org/ServeContent?doi=10.3987%2Fcom-00-9014 10.1073/pnas.93.23.13143 1. S. J. Darkin-Rattray, A. M. Gurnett, R. W. Myers, P. M. Dulski, T. M. Crumley, J. J. Allocco, C. Cannova, P. T. Meinke, S. L. Colletti, M. A. Bednarek, S. B. Singh, M. A. Goetz, A. W. Dombrowski, J. D. Polishook, and D. M. Schmatz, Proc. Natl. Acad. Sci. USA, 1996, 93, 13143. 10.1016/0040-4039(96)01844-8 2. S. B. Singh, D. L. Zink, J. D. Polishook, A. W. Dombrowski, S. J. Darkin-Rattray, D. M. Schmatz, and M. A. Goetz, Tetrahedron Lett., 1996, 37, 8077. 10.7164/antibiotics.29.1 a) N. Tsuji, M. Kobayashi, K. Nagashima, Y. Wakisaka, and K. Koizumi, J. Antibiot., 1976, 29, 1; 10.1016/S0021-9258(17)44885-X b) M. Yoshida, M. Kijima, M. Akita, and T. Beppu, J. Biol. Chem., 1990, 265, 17174. 10.1016/0040-4020(82)85043-6 4. J. M. Liesch, C. C. Sweeley, G. D. Staffeld, M. S. Anderson, D. J. Weber, and R. P. Scheffer, Tetrahedron, 1982, 38, 45. 10.1016/S0040-4039(00)88171-X 5. Chlamydocin and its analogues a) U. Schmidt, T. Beuttler, A. Lieberknecht, and H. Griesser, Tetrahedron Lett., 1983, 24, 3573; b) U. Schmidt, A. Lieberknecht, H. Griesser, and F. Bartkowiak, Angew. Chem., Int. Ed. Engl., 1984, 23, 318; c) U. Schmidt, A. Lieberknecht, H. Griesser, R. Utz, T. Benttler, and F. Bartkowiak, Synthesis, 1986, 361; d) R. E. Shute, B. Dunlap, and D. H. Rich, J. Med. Chem., 1987, 30, 71; e) J. E. Baldwin, R. M. Adlington, C. R. A. Godfrey, and V. K. Patel, Tetrahedron, 1993, 49, 7837; f) E. Bernardi, S. Cros, P. Viallefont, and R. Lazaro, Bull. Soc. Chim. Fr., 1994, 131, 944. 10.1016/S0040-4039(00)96315-9 6. HC toxin and its analogues a) R. Jacquier, R. Lazaro, H. Raniriseheno, and PH. Viallefont, Int. J. Peptide Protein Res., 1987, 30, 22; b) R. E. Shute, and D. H. Rich, Tetrahedron Lett., 1987, 28, 3419; c) see also ref. 5. d),. 10.1002/anie.198903331 7. WF-3161 U. Schmidt, U. Beutler, and A. Lieberknecht, Angew. Chem., Int. Ed. Engl., 1989, 28, 333. 10.1021/ja9615841 8. Trapoxin J. Taunton, J. L. Collins, and S. L. Schreiber, J. Am. Chem. Soc., 1996., 118, 10412. 10.1021/ja990918u 9. D. L. Boger, H. Keim, B. Oberhauser, E. P. Schreiner, and C. A. Foster, J. Am. Chem. Soc., 1999, 121, 6197. 10.1021/ja00249a031 10. L. D. Arnold, J. C. G. Drover, and J. C. Vederas, J. Am. Chem. Soc., 1987, 109, 4649. 10.1139/v86-113 11. S. E. Ramer, R. N. Moore, and J. C. Vederas, Can. J. Chem., 1986, 64, 706. 10.1021/jo00367a033 12. P. G. McDougal, J. G. Rico, Y.-I. Oh, and B. D. Condon, J. Org. Chem., 1986, 51, 3388. 10.1016/S0040-4039(00)93583-4 a) S. Chen and J. Xu, Tetrahedron Lett., 1991, 32, 6711; 10.1080/00397919308009787 b) J. D udash, Jr., J. J. Scott, C. Mayer, and M. M. Joullie, Syn. Commun., 1993, 23, 349. 10.1039/c39870001625 14. W. P. Griffith, S. V. Ley, G. P. Whitcombe, and A. D. White, J. Chem. Soc., Chem. Commun., 1987, 1625. 10.1021/ja00952a026 15. a) K. E. Pfitznier and J. G. Moffatt, J. Am. Chem. Soc., 1965, 87, 5661 and 5670; b) see also ref. 8,. 10.1021/jo00170a070 16. D. B. Dess and J. C. Martin, J. Org. Chem., 1983, 48, 4155. 17. Apicidin mp 186-188°C; 1H NMR (300 MHz, CDCl3): 7.56 (1H, d, J = 7.8 Hz), 7.39 (1H, d, J = 8.1 Hz), 7.00 — 7.30 (4H, m), 6.46 (1H, d, J = 10.2 Hz), 6.42 (1H, d, J = 6 Hz), 5.06 (1H, d, J = 4.5 Hz), 4.73 (1H, t, J = 10.5 Hz), 4.18 (1H, dt, J = 7.5, 10.0 Hz), 3.90 — 4.10 (2H, m), 4.03 (3H, s), 3.79 (1H, dd, J = 10.5, 10 Hz), 3.45 (1H, dd, J = 6.0, 15.0 Hz), 3.05 (1H, dt, J = 2.4, 13.0 Hz), 2.39 ( 2H, q, J = 7.5 Hz), 2.36 (2H, t, J = 7.5 Hz), 1.05 — 2.20 (17H, m), 1.04 (3H, t, J = 7.5 Hz), 0.92 (3H, t, J = 7.5 Hz), 0.86 (3H, d, J = 6.6 Hz); IR (film) 3271, 1713, 1694, 1667, 1616 cm-1; HRMS (FAB, NBA) MH+ calcd for C34H50 N5O6 624.3761, found 624.3718; [α]28D -82.6o (c 0.25, CHCl3)