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Simple, Catalytic Enantioselective Syntheses of Estrone and Desogestrel
Hu, Qi-Ying,Rege, Pankaj D.,Corey
, p. 5984 - 5986 (2007/10/03)
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 α,β-enal 6 via intermediates 8 and 9. Desogestrel was synthesized using a similar strategy from diene 5 and α,β-enal 11 via intermediates 12-17. The efficient syntheses of the chiral catalyst 2 and its enantiomer are also presented. Copyright
