Preparation of the synthetic equivalents of chiral cyclohexadienone and cycloheptadienone: The enantio- and diastereo-controlled synthesis of (-)- clavularin B

Synlett

Volumn , Issue 5, 1999, Pages 529-532

  Hiroya, Kou ^a   Zhang, Huilan ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

(+) clavularin B; Chiral building block; Cycloheptadienone synthon; Cyclohexadienone synthon; Lipase mediated resolution

Indexed keywords

ALKADIENE; CLAVULARIN B; CYCLOHEPTANE DERIVATIVE; CYCLOHEXANE DERIVATIVE; MARINE TOXIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATIONAL TRANSITION; DIASTEREOISOMER; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; THERMOSTABILITY;

EID: 0032962125     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2692     Document Type: Article

References (21)

1. Ogasawara, K. Pure Appl. Chem. 1994, 66, 2119.
2. Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.; Ogasawara, K. Synthesis 1993, 948.
3. Ogasawara, K. J. Syn. Org. Chem. Jpn. 1996, 54, 29.
4. Tanaka, K.; Ogasawara, K. Synthesis 1995, 1237.
5. Takano, S.; Moriya, M.; Kamikubo, T.; Hiroya, K.; Ogasawara, K. Tetrahedron Lett. 1993, 34, 8485.
6. Luche, J. -L. J. Am. Chem. Soc. 1978, 100, 2226: Gemal, A. L.; Luche, J. -L. J. Am. Chem. Soc. 1981, 103, 5454.
7. Luche, J. -L. J. Am. Chem. Soc. 1978, 100, 2226: Gemal, A. L.; Luche, J. -L. J. Am. Chem. Soc. 1981, 103, 5454.
8. Krabbenhoft, H. O. J. Org. Chem. 1979, 44, 4285.
9. 13C NMR(75 MHz) δ :208.77, 206.30, 145.89, 131.98, 59.32, 41.57, 34.58, 33.30, 29.99, 27.59, 24.49, 19.86.
10. Takano, S; Inomata, K.; Ogasawara, K. Chem. Lett. 1989, 359.
11. Horiguchi, Y.; Matsuzawa, S.; Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 4025.
12. McWilliams, J. C.; Clardy, J. J. Am. Chem. Soc. 1994, 116, 8378.
13. Weinmann, H.; Winterfeldt, E. Synthesis 1995, 1094.
14. Endo, M.; Nakagawa, M.; Hamamoto, Y.; Nakanishi, T. J. Chem. Soc., Chem. Commun. 1983, 322 and 980.
15. Kobayashi, M.; Son, B. W.; Kido, M.; Kyogoku, Y.; Kitagawa, I. Chem. Pharm. Bull. 1984, 31, 2160.
16. Boeckman, Jr. R. K.; Blum, D. M.; Ganem, B.; Halvey, N. Org. Synth. Col. Vol. 1988, 6, 1033.
17. Narasaka, K.; Soai, K.; Mukaiyama, T. Chem. Lett. 1974, 1223: Narasaka, K.; Soai, K.; Akiyama, Y.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1976, 49, 779.
18. Narasaka, K.; Soai, K.; Mukaiyama, T. Chem. Lett. 1974, 1223: Narasaka, K.; Soai, K.; Akiyama, Y.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1976, 49, 779.
19. Chiral synthesis of clavularin A: (a) Tamura, R.; Watabe, K.; Ono, N.; Yamamoto, Y. J. Org. Chem. 1993, 58, 4471.
20. (b) Ref. 12.
21. Ureth, R. J. Chem. Soc., Chem. Commun. 1984, 989.