Total syntheses of (+)-Fawcettimine and (+)-Lycoposerramine-B

Journal of Organic Chemistry

Volumn 75, Issue 10, 2010, Pages 3420-3426

  Otsuka, Yasunari ^a   Inagaki, Fuyuhiko ^a   Mukai, Chisato ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EFFICIENT CONSTRUCTION; LYCOPOSERRAMINE-B; MITSUNOBU REACTIONS; STEREOSELECTIVE MANNER; SYNTHETIC INTERMEDIATES; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

ALKALOID DERIVATIVE; AZONANE; FAWCETTIMINE; LYCOPOSERRAMINE; LYCOPOSERRAMINE B; OXATRICYCLO[7.3.0.0 1,5]DODECANEDIONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; MITSUNOBU REACTION; STEREOCHEMISTRY; SYNTHESIS;

ALKALOIDS; HETEROCYCLIC COMPOUNDS, 3-RING; MOLECULAR CONFORMATION; OXIMES; STEREOISOMERISM;

EID: 77952522484     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100499h     Document Type: Article

References (34)

1. Burnell, R. H. J. Chem Soc. 1959, 3091-3093
2. Burnell, R. H.; Mootoo, B. S. Can. J. Chem. 1961, 39, 1090-1093
3. Burnell, R. H.; Chin, C. G.; Mootoo, B. S.; Taylor, D. R. Can. J. Chem. 1963, 41, 3091-3094
4. Ma, X.; Gang, D. R. Nat. Prod. Rep. 2004, 21, 752-772
5. Inubushi, Y.; Ishii, H.; Harayama, T.; Burnell, R. H.; Ayer, W. A.; Altenkirk, B. Tetrahedron Lett. 1967, 1069-1072
6. Nishio, K.; Fujiwara, T.; Tomita, K.; Ishii, H.; Inubushi, Y.; Harayama, T. Tetrahedron Lett. 1969, 861-864
7. Inubushi, Y.; Harayama, T.; Yamaguchi, K.; Ishii, H. Chem. Pharm. Bull. 1981, 29, 3418-3420
8. Harayama, T.; Takatani, M.; Inubushi, Y. Tetrahedron Lett. 1979, 20, 4307-4310
9. Harayama, T; Takatani, M.; Inubushi, Y. Chem. Pharm. Bull. 1980, 28, 2394-2402
10. Heathcock, C. H.; Smith, K. M.; Blumenkopf, T. A. J. Am. Chem. Soc. 1986, 108, 5022-5024
11. Heathcock, C. H.; Blumenkopf, T. A.; Smith, K. M. J. Org. Chem. 1989, 54, 1548-1562
12. Linghu, X.; Kennedy-Smith, J. J.; Toste, F. D. Angew. Chem., Int. Ed. 2007, 46, 7671-7673
13. For the synthetic studies of fawcettimine, see: Mehta, G.; Reddy, M. S.; Radhakrishnan, R.; Manjula, M. V.; Viswamitra, M. A. Tetrahedron Lett. 1991, 32, 6219-6222
14. Liu, K.-M.; Chau, C.-M.; Sha, C.-K. Chem. Commun. 2008, 91-93
15. Katakawa, K.; Kitajima, M.; Aimi, N.; Seki, H.; Yamaguchi, K.; Furihata, K.; Harayama, T.; Takayama, H. J. Org. Chem. 2005, 70, 658-663
16. Inubushi, Y.; Ishii, H.; Yasui, B.; Hashimoto, M. Tetrahedron Lett. 1966, 7, 1537-1549
17. Inubushi, Y.; Ishii, H.; Harayama, T. Tetrahedron Lett. 1966, 7, 1551-1559
18. Inubushi, Y.; Ishii, H.; Yasui, B.; Hashimoto, M.; Harayama, T. Chem. Pharm. Bull. 1968, 16, 82-91
19. Inubushi, Y.; Ishii, H.; Yasui, B.; Hashimoto, M.; Harayama, T. Chem. Pharm. Bull. 1968, 16, 92-100
20. Inubushi, Y.; Ishii, H.; Yasui, B.; Harayama, T. Chem. Pharm. Bull. 1968, 16, 101-112
21. Kozaka, T.; Miyakoshi, N.; Mukai, C. J. Org. Chem. 2007, 72, 10147-10154
22. In the previous three total syntheses, (5-7) construction of the azonane ring was attained in moderate yields.
23. During this program ongoing, Takayama reported the similar Mitsunobu reaction for the formation of the azonane framework in the total synthesis of lycoposerramine-C and phlegmariurine-A; see: Nakayama, A.; Kogure, N.; Kitajima, M.; Takayama, H. Org. Lett. 2009, 11, 5554-5557
24. Arhart, R. J.; Martin, J. C. J. Am. Chem. Soc. 1972, 94, 5003-5010
25. Kuramochi, A.; Usuda, H.; Yamatsugu, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 14200-14201
26. Tokumaru, K.; Arai, S.; Nishida, A. Org. Lett. 2006, 8, 27-30
27. Boeckman, R. K., Jr.; Potenza, J. C. Tetrahedron Lett. 1985, 26, 1411-1414
28. Spectral analysis of the isolated products tentatively indicated that the Ns group was converted into some functionality, although their structures are uncertain yet.
29. Kan, T.; Fukuyama, T. Chem. Commun. 2004, 353-359
30. The synthetic (+)-fawcettimine (1) was identical with the natural compound by comparison with their spectral data.
31. The synthetic 21 was identical with the compound (9) derived from (-)-serratinine, by comparison of their spectral data.
32. The synthetic (+)-lycoposerramine-B (3) was identical with the natural compound (9) by comparison of their spectral data.
33. D value of the natural lycoposerramine-B is available, although its CD spectral data were recorded. (9)
34. 2 and aqueous 3 M NaOH; see: Kabalka, G. W.; Shoup, T. M.; Goudgaon, N. M. J. Org. Chem. 1989, 54, 5930-5933