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Elsevier, Tetrahedron, 11(55), p. 3255-3264

DOI: 10.1016/s0040-4020(98)01138-7

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Improved syntheses of aromatase inhibitors and neuroactive steroids efficient oxidations and reductions at key positions for bioactivity

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This paper is available in a repository.

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Abstract

An Henbest reduction, followed by the preparation of a silyl enol ether and oxidation in situ with m-CPBA has led to the neurosteroids 3[alpha]-hydroxy- and 3[alpha],21-dihydroxy-5[alpha]-pregnanolones. Using testosterone as starting material, a new short synthesis of an aromatase inhibitor, 4-OHA, has been achieved through hydroboration/oxidation followed by a Swern type oxidation and epimerization. Another aromatase inhibitor, androst-4-ene-3,6-17-trione, has been efficiently prepared using PCC on montmorillonite K10, under ultrasonic irradiation. ; http://www.sciencedirect.com/science/article/B6THR-3WC46V7-8/1/5f915790e78df65f4c988ab78bf4f174