期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 14, 期 5, 页码 1541-1551出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200700182
关键词
Birch reduction; contraceptives; Heck reaction; palladium; steroids
A novel enantioselective total synthesis of the oral contraceptive desogestrel (2) is described, in which the tetracyclic steroid core is formed by a sequence of two consecutive Heck reactions. Conversion of the known enantiopure diketone 7 led to the chiral bicycle 6 which was used for a diastereoselective intermolecular Heck reaction with vinyliodide 5 to give 15. In the following intramolecular Heck reaction, the tetracyclic ring system was formed to give 4, from which the synthesis of desogestrel (2) was furnished.
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