Synthetic study of pinnatoxin A: Intramolecular Diels-Alder approach to the AG-ring

Synlett

Volumn , Issue 6, 1999, Pages 692-694

  Ishiwata, Akihiro ^a   Sakamoto, Satoshi ^a   Noda, Takeshi ^a   Hirama, Masahiro ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Ca2+channel; Convergent synthesis; Diastereoselectivity; Intramolecular Diels Alder reaction; Pinnatoxin A

Indexed keywords

CALCIUM CHANNEL; MARINE TOXIN; PINNATOXIN A; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; ESTERIFICATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0033036264     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2743     Document Type: Article

References (26)

1. a) D. Uemura, T. Chou, T. Haino, A. Nagatsu, S. Fukuzawa, S. Zheng, H. Chen, J. Am. Chem. Soc., 1995, 117, 1155.
2. b) T. Chou, O. Kamo, D. Uemura, Tetrahedron Lett., 1996, 37, 4023.
3. For spirolides, see: a) T. Hu, J. M. Curtis, Y. Oshima, M. A. Quilliam, J. A. Walter, W. Watson-Wright, J. L. C. Wright, J. Chem. Soc., Chem. Commun, 1995, 2159.
4. b) T. Hu, J. M. Curtis, J. A. Walter, J. L. C. Wright, Tetrahedron Lett., 1996, 37, 7671.
5. For gymnodimines, see: a) T. Seki, M. Satake, L. Mackenzie, H. F. Kaspar, T. Yasumoto, Tetrahedron Lett., 1995, 36, 7093.
6. b) M. Stewart, J. W. Blunt, M. H. G. Munro, W. T. Robinson, D. J. Hannah, Tetrahedron Lett., 1997, 38, 4889.
7. S. Z. Zheng, F. L. Huang, S. C. Chen, X. F. Tan, J. B. Zuo, J. Peng, R. W. Xie, Zhongguo Haiyang Yaowu (Chinese J. of Marine Drugs), 1990, 33, 33.
8. J. A. McCauley, K. Nagasawa, P. A. Lander, S. G. Mischke, M. A. Semones, Y. Kishi, J. Am. Chem. Soc., 1998, 120, 7647.
9. T. Noda, A. Ishiwata, S. Uemura, S. Sakamoto, M. Hirama, Synlett, 1998, 298.
10. T. Sugimoto, J. Ishihara, A. Murai, Tetrahedron Lett., 1997, 38, 7379; J. Ishihara, T. Sugimoto, A. Murai, Synlett, 1998, 603.
11. T. Sugimoto, J. Ishihara, A. Murai, Tetrahedron Lett., 1997, 38, 7379; J. Ishihara, T. Sugimoto, A. Murai, Synlett, 1998, 603.
12. 2 (95%).
13. A. Pfalts, A. Mattenberger, Angew. Chem. Int. Ed. Engl., 1982, 21, 71.
14. a) A. Eschenmoser, Angew. Chem. Int. Ed. Engl., 1971, 10, 330.
15. b) S. Takano, K. Inamata, K. Samizu, S. Tomita, M. Yanase, M. Suzuki, Y. Iwabuchi, Chem. Lett., 1989, 1283
16. 4 (2 eq), MeOH in 25% yield (3 steps).
17. Y. Oikawa, T. Nishi, O. Yonemitsu, Tetrahedron Lett., 1983, 24, 4037.
18. 2POMe (1.6 eq), n-BuLi (1.5 eq), THF, -78 - 50°C (96%).
19. M. A. Blanchette, W. Choy, J. T. Davis, A. P. Essenfeld, S. Masamune, W. R. Roush, T. Sakai, Tetrahedron Lett., 1984, 25, 2183.
20. H. Köster and N. D. Shinha, Tetrahedron Lett., 1982, 23, 2641.
21. O. Mitsunobu, Synthesis, 1981, 1.
22. W. R. Roush, In Comprehensive Organic Synthesis; B. M. Trost; I. Fleming; L. A. Paquette, Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 513; W.R. Roush, B. B. Brown, J. Am. Chem. Soc., 1993, 115, 2268.
23. W. R. Roush, In Comprehensive Organic Synthesis; B. M. Trost; I. Fleming; L. A. Paquette, Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 513; W.R. Roush, B. B. Brown, J. Am. Chem. Soc., 1993, 115, 2268.
24. a) K. Maruoka, K. Nonoshita, H. Yamamoto, Synth Commun, 1988, 18, 1453.
25. b) H. Lamy-Schelkens, D. Giomi, L. Ghosez, Tetrahedron Lett., 1989, 30, 5887.
26. 3). (matrix presented)