Synthesis of unusual cholestane analogs by Diels-Alder reaction (A+CD → ABCD)

Tetrahedron Letters

Volumn 38, Issue 12, 1997, Pages 2155-2158

  De Riccardis, Francesco ^a   Izzo, Irene ^a   Tedesco, Consiglia ^a   Sodano, Guido ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLESTANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

BETULACEAE;

EID: 0031585070     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00270-0     Document Type: Article

References (13)

1. 1. Akhrem, A.A.; Titov, Y. A. Total Synthesis of Steroids, Israel Program for Scietific Translations, Jerusalem, 1969.
2. 2. Dane, E. Angew. Chem. 1939, 52, 655. For a recent enantioselective version of this reaction see: Quinkert, G.; del Grosso, M.; Bucher, A.; Bauch, M.; Doring, W.; Bats, J.W.; Durner, G. Tetrahedron Lett. 1992, 33, 3617.
3. 2. Dane, E. Angew. Chem. 1939, 52, 655. For a recent enantioselective version of this reaction see: Quinkert, G.; del Grosso, M.; Bucher, A.; Bauch, M.; Doring, W.; Bats, J.W.; Durner, G. Tetrahedron Lett. 1992, 33, 3617.
4. 3. Fringuelli, F.; Taticchi, A. Dienes in the Diels-Alder Reaction, John Wiley & Sons, New York, 1990.
5. 4. De Riccardis, F.; Spinella, A.; Izzo, I.; Giordano, A.; Sodano G. Tetrahedron Lett. 1995, 36, 4303.
6. +), 417, 319.
7. w = 0.046, All calculations were perfomed using the TEXSAN crystallographic software package by Molecular Structure Corporation.
8. 7. Kolaczkowski, L.; Reusch, W. J. Org. Chem. 1985, 50, 4766, and references therein.
9. +), 367, 339, 269.
10. +), 641, 543.
11. +), 721.
12. 11. For a review see: Jensen, A. W.; Wilson, S.R.; Schuster, D.I. Bioorg. Med. Chem. 1996, 4, 767.
13. 12. Tsuda, M.; Ishida, T.; Nogami, T.; Kurono, S.; Ohashi, M. J. Chem. Soc. Chem. Comm. 1993, 1296.