Concurrent resolution and oxidation of an allylic acetate and its utilization in the diastereocontrolled synthesis of some cyclopentanoid monoterpenes

Tetrahedron Letters

Volumn 40, Issue 36, 1999, Pages 6617-6620

  Nagata, Hiroshi ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Enzymatic reaction; Enzymes; Oxidation; Palladium; Palladium compounds; Resolution; Terpenes; Terpenoids

Indexed keywords

4 ACETOXYBICYCLO[3.2.1]OCT 2 ENE; ACETIC ACID DERIVATIVE; BICYCLO[3.2.1]OCT 3 EN 2 ONE; BUFFER; DIHYDRONEPENTALACTONE; IRIDOMYRMECIN; ISOIRIDOMYRMECIN; MITSUGASHIWALACTONE; PALLADIUM COMPLEX; TERPENE DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOMER; OXIDATION; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0033520275     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01321-0     Document Type: Article

References (19)

1. Pertinent reviews, see: Grayson, D. H. Nat. Prod. Rep. 1998, 14, 439, and previous reports.
2. (a) Kawamura, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1995, 2403.
3. (b) Nagata, H.; Taniguchi, T.; Kawamura, M.; Ogasawara, K. Tetrahedron Lett. 1999, 40, 4207.
4. (a) Allen, J. V.; Williams, J. M. J. Tetrahedron Lett. 1996, 37, 1859.
5. (b) Stürmer, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1173.
6. (c) Larsson, A. L. E.; Persson, B. A.; Bäckvall, J.-E. Angew. Chem., Int. Ed. Engl. 1997, 36, 1211.
7. (d) Jones, M. M.; Williams, J. M. J. Chem. Commun. 1998, 2519.
8. Palladium-catalyzed allylic alcohol oxidation, see: (a) Kaneda, K.; Fujii, M.; Morioka, K. J. Org. Chem. 1996, 61, 4502.
9. ( b) Kaneda, K.; Fujie, Y.; Ebitani, K. Tetrahedron Lett. 1997, 52, 9023.
10. (c) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011.
11. (d) Hayashi, M.; Yamada, K; Arikita, O. Tetrahedron Lett. 1999, 40, 1171.
12. Previous synthesis: Yamane, T.; Takahashi, M.; Ogasawara, K. Synthesis 1995, 444.
13. Sakan, T.; Murai, F.; Asoe, S.; Hyeon, S. B.; Hayashi, Y. J. Chem. Soc. Jpn. 1969, 90, 507.
14. Takai, K.; Hotta, Y.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1980, 53, 1698.
15. Suemune, H.; Oda, K.; Saeki, S.; Sakai, K. Chem. Pharm. Bull. 1988, 36, 172.
16. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392.
17. Shibuya, K.; Nagaoka, H.; Yamada, Y. J. Chem. Soc., Chem. Commun. 1991, 1545.
18. Takahashi, Y.; Tanaka, M.; Wu, X.-M.; Sakai, K. Nat. Prod. Lett. 1992, 1, 217.
19. Cavill, G. W. K.; Ford, D. L.; Locksley, H. D. Aust. J. Chem. 1956, 9, 288.