Short total synthesis of (+)-madindolines A and B

Organic Letters

Volumn 4, Issue 4, 2002, Pages 501-503

  Hirose, Tomoyasu ^a   Sunazuka, Toshiaki ^a   Shirahata, Tatsuya ^a   Yamamoto, Daisuke ^a   Harigaya, Yoshihiro ^a   Kuwajima, Isao ^a   Omura, Satoshi ^a  

^a KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FUSED HETEROCYCLIC RINGS; INDOLE DERIVATIVE; INTERLEUKIN 6; MADINDOLINE A;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DRUG ANTAGONISM; STEREOISOMERISM; SYNTHESIS;

BICYCLO COMPOUNDS, HETEROCYCLIC; CYCLIZATION; INDICATORS AND REAGENTS; INDOLES; INTERLEUKIN-6; MODELS, MOLECULAR; STEREOISOMERISM;

EID: 0037149025     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017058i     Document Type: Article

References (21)

1. Hayashi, M.; Kim, Y.-P.; Takamatsu, S.; Enomoto, A.: Shinose, M.; Takahashi, Y.; Tanaka, H.; Komiyama, K.; Ōmura, S. J. Antibiot. 1996, 49, 1091-1095.
2. Takamatsu, S.; Kim, Y.-P.; Enomoto, A.; Hayashi, M.; Tanaka, H.; Komiyama, K.; Ōmura, S. J. Antibiot. 1997, 50, 1069-1072.
3. Sunazuka, T.; Hirose, T.; Shirahata, T.; Harigaya, Y.; Hayashi, M.; Komiyama, K.; Ōmura, S.; Smith, A. B., III. J. Am. Chem. Soc. 2000, 122, 2122-2123.
4. For another total synthesis of madindoline A, see: Hosokawa, S.; Sekiguchi, K.; Hayase, K.; Hirukawa, Y.; Kobayashi, S. Tetrahedron Lett. 2000, 41, 6435-6439.
5. Mori, K.; Koseki, K. Tetrahedron 1988, 44, 6013-6020.
6. Michael addition of (-)-6 to methyl methacrylate or acrylate to afford 9 was unsuccessful under several conditions.
7. (a) Ramanjulu, J. M.; Joullié, M. M. Synth. Commun. 1996, 26, 1379-1384.
8. (b) Abdel-Magid, A. F.; Maryanoff, C. A.; Carson, K. G. Tetrahedron Lett. 1990, 31, 5595-5598.
9. Narasaka, K.; Morikawa, A.; Saigo, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 2773-2776.
10. Hosomi, A.; Hashimoto, H.; Sakurai, H. Tetrahedron Lett. 1980, 21, 951-954.
11. Martin, H.; Hoffmann, R.; Rabe, J. J. Org. Chem. 1985, 50, 3849-3859.
12. (E)-Isomers changed to more thermodynamically stable (Z)-isomers during the reaction.
13. The Z-stereochemistry for 12 and 15 was determined by NOE as show here.
14. Still, W. C. J. Org. Chem. 1985, 41, 3063-3064.
15. During the formation of the enolate of 9, the chiral center of 5 is destroyed. So, it is not necessary to employ the optical active 5. We used the chiral form of 5 in order to get the data of compounds 7, 8, and 9 easily.
16. When we used KDA for the formation of its enolate, the selectivity was 2:1. Also, when we used LDA in the presence of HMPA, the selectivity was 2.3:1. On the basis of these results, there should be chelation during enolate formation of ester 9.
17. (a) Fujita, M.; Obayashi, M.; Hiyama, T. Tetrahedron 1988, 44, 4135-4145.
18. (b) Scheidt, K. A.; Chen, H.; Follows, B. C.; Chemler, S. R.; Coffey, D. S.; Roush, W. R. J. Org. Chem. 1998, 63, 6436-6437.
19. (a) Pilcher, A. S.; DeShong, P. J. Org. Chem. 1996, 61, 6901-6905.
20. (b) Pilcher, A. S.; Ammon, H. L.; DeShong, P. J. Am. Chem. Soc. 1995, 117, 5166-5167.
21. Hayashi, M.; Fukami, A.; Rho, M.-C.; Sekiguchi, Y.; Sunazuka, T.; Hirose, T.; Komiyama, K.; Ōmura, S. Proc. Natl. Acad. Sci. U.S.A. In preparation.