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Highly efficient Lewis acid catalyzed, one step conversions of 16α,17α-epoxy-3β-hydroxypregn-5-en-20-one to d-homosteroid and Δ13-steroids by Navdeep K Girdhar; M.P.S Ishar; Rajiv Kumar; Rajinder Singh; Gurmit Singh is a Chemistry article available to read on EtoBox.

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AbstractÐConversion of 16a,17a-epoxy-3b-hydroxypregn-5-en-20-one (1a) to 16b-chloro-3b,17a-dihydroxy-17b-methyl-17a-homoandrost-5-en-17a-one (3) in very high yields (95%), in one step by treatment with 3 equiv. of anhyd. AlCl 3 , has been achieved; use of two equiv. of AlCl 3 affords mixture of d-homosteroid 3 (70%) and chlorohydrin 4 (27%). On the other hand, treatment of 1a with excess of acetic anhydride and anhydrous ZnCl 2 at room temperature leads to reversal of the direction of epoxide ring opening with concomitant methyl migration, leading to 3b,16a-diacetoxy-17-methyl-17a-pregna-5,13-diene-20-one (6) in high yield (92 %). The conversions are a remarkable improvement over related routes in terms of both yield and selectivity.

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Author

Navdeep K Girdhar; M.P.S Ishar; Rajiv Kumar; Rajinder Singh; Gurmit Singh

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

2001

Language

EN

Field

Chemistry (Physical Sciences)