Simple, catalytic enantioselective syntheses of estrone and desogestrel.
Highly enantioselective and very short syntheses of the bioactive forms of estrone (3) and desogestrel (4) are described using a chiral oxazaborolidinium catalyst (2) in the key initial step. Enantiomerically pure estrone was synthesized in eight steps from the readily available starting materials diene 5 and alpha,beta-enal 6 via intermediates 8 and 9. Desogestrel was synthesized using a similar strategy from diene 5 and alpha,beta-enal 11 via intermediates 12-17. The efficient syntheses of the chiral catalyst 2 and its enantiomer are also presented.
Hu
Qi-Ying
QY
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Rege
Pankaj D
PD
Corey
E J
EJ
D000605:Amino Alcohols / Q000737:chemistry; D002384:Catalysis; D017135:Desogestrel / Q000138:chemical synthesis*; D004970:Estrone / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D045167:Progesterone Congeners / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000605:Amino Alcohols; D007202:Indicators and Reagents; D045167:Progesterone Congeners; D004970:Estrone; D017135:Desogestrel