A convenient synthesis of (+)-albicanol based on enzymatic function: Total syntheses of (+)-albicanyl acetate, (-)-albicanyl 3,4- dihydroxycinnamate, (-)-drimenol, (-)-drimenin and (-)-ambrox

Tetrahedron Asymmetry

Volumn 11, Issue 6, 2000, Pages 1375-1388

  Akita, Hiroyuki ^a   Nozawa, Masako ^a   Mitsuda, Ayumi ^a   Ohsawa, Hitomi ^a  

^a TOHO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; AMBERGRIS; CINNAMIC ACID DERIVATIVE; NATURAL PRODUCT; SESQUITERPENE DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ACETYLATION; ALCALIGENES; ARTICLE; ENANTIOMER; ENZYME ACTIVITY; NONHUMAN; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034615857     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00076-8     Document Type: Article

References (18)

1. Jansen, B. J. M.; De Groot, A. Nat. Prod. Rep. 1991, 309-318, and references cited therein.
2. Jansen, B. J. M.; De Groot, A. Nat. Prod. Rep. 1991, 319-337, and references cited therein.
3. (a) Barrero, A. F.; Alvarez-Manzaneda, E.; Altarejos, J.; Salido, S.; Ramos, J. M.; Simmonds, M. S. J.; Blaney, W. M. Tetrahedron Lett. 1994, 35, 2945-2948.
4. (b) Barrero, A. F.; Alvarez-Manzaneda, E.; Altarejos, J.; Salido, S.; Ramos, J. M. Tetrahedron 1995, 51, 7435-7450.
5. Okawara, H.; Nakai, H.; Ohno, M. Tetrahedron Lett. 1982, 23, 1087-1090.
6. Shishido, K.; Tokunaga, Y.; Omachi, N.; Hiroya, K.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1990, 2481-2486.
7. Cortes, M. J.; Razmilic, I.; Sierra, J. R.; Lopez, J. Chem. Ind. 1985, 735.
8. Oyarzun, M. L.; Cortes, M.; Sierra, J. Synth. Commun. 1982, 12, 951-958.
9. Cortes, M.; Razmilic, I.; Lopez, J. J. Nat. Prod. 1990, 53, 1369-1371.
10. Liapis, M.; Ragoussis, V. J. Chem. Soc., Perkin Trans. 1 1985, 815-817.
11. (a) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.
12. (b) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.
13. Hellou, J.; Andersen, R. J.; Thompson, J. E. Tetrahedron 1982, 38, 1875-1879.
14. Liapis, M.; Ragoussis, V. J. Chem. Soc., Perkin Trans. 1 1987, 987-992.
15. Appel, H. H.; Brooks, C. J. W.; Overton, K. H. J. Chem. Soc. 1959, 3322-3332.
16. Toyota, M.; Asakawa, Y.; Takemoto, T. Phytochemistry 1981, 20, 2359-2366.
17. Appel, H. H.; Connolly, J. D.; Overton, K. H. (in part); Bond, R. P. M. J. Chem. Soc. 1960, 4685-4692.
18. Akita, H.; Nozawa, M.; Shimizu, H. Tetrahedron: Asymmetry 1998, 9, 1789-1799, and references cited therein.