Simple, catalytic enantioselective syntheses of estrone and desogestrel |
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Authors: | Hu Qi-Ying Rege Pankaj D Corey E J |
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Institution: | Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. |
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Abstract: | 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. |
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