Stereo and chemical course of acid-catalyzed double bond migration of cholesta-5,7-dien-3β-ol to 5α-cholesta-8,14-dien-3β-ol

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 11, 2000, Pages 1697-1703

  Seto, Hideharu ^a   Fujioka, Shozo ^b   Koshino, Hiroyuki ^a   Takatsuto, Suguru ^b   Yoshida, Shigeo ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^b JOETSU UNIVERSITY OF EDUCATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; CATALYSIS; CHEMICAL BONDS; ETHANOL; HYDROCHLORIC ACID; STEREOCHEMISTRY;

STEREOSELECTIVITY;

UNSATURATED COMPOUNDS;

EID: 0034616726     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b001726o     Document Type: Article

References (11)

1. M. Fieser, W. E. Rosen and L. F. Fieser, J. Am. Chem. Soc., 1952, 74, 5397.
2. L. F. Fieser and G. Ourisson, J. Am. Chem. Soc., 1953, 75, 4404.
3. F. Gautschi and K. Bloch, J. Biol. Chem., 1958, 233, 1343.
4. I. A. Watkinson, D. C. Wilton, K. A. Munday and M. Akhtar, Biochem. J., 1971, 121, 131.
5. Y.-K. Paik, J. M. Trzaskos, A. Shafiee and J. L. Gaylor, J. Biol. Chem., 1984, 259, 13413.
6. M. Taton, P. Benveniste and A. Rahier, Eur. J. Biochem., 1989, 185, 605.
7. J.-C. Jang, S. Fujioka, M. Tasaka, H. Seto, S. Takatsuto, A. Ishii, M. Aida, S. Yoshida and J. Sheen, Genes Dev., in the press.
8. H. W. Kircher and F. U. Rosenstein, Lipids, 1974, 9, 333.
9. H. W. Kircher, Lipids, 1974, 9, 623.
10. R. M. Kellogg, in Comprehensive Organic Syntheses, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 8, pp. 79-106; and references cited therein.
11. E. J. Taylor and C. Djerassi, J. Org. Chem., 1977, 42, 3571.