Preparation of a functionalized tetracyclic intermediate for the synthesis of rhodexin A |
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Authors: | Jung Michael E Chu Hiufung V |
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Affiliation: | Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA. jung@chem.ucla.edu |
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Abstract: | An efficient synthesis of the tetracyclic steroid core, 19, of rhodexin A and sarmentogenin is reported. An initial inverse-electron-demand Diels-Alder reaction of the acyldiene 6 with the silyl enol ether 7a gave the cycloadduct 8 with the required four contiguous stereocenters in a single step. This compound was then transformed into the methylated enedione 13 which afforded after a reductive alkylation and annulation sequence the tetracycle 19. |
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