Photoinduced molecular transformations. Part 112. Transformation of steroids into ring-A-aromatized steroids and 19-norsteroids involving a regioselective β-scission of alkoxyl radicals; synthesis of two marine natural products, 19-nor-5α-cholestan-3β-ol and 19-norcholest-4-en-3-one, and new synthesis of estrone and 19-nortestosterone
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 2199-2205
- https://doi.org/10.1039/p19900002199
Abstract
A new transformation of steroids into 19-norsteroids and ring-A-aromatized steroids is described. The transformation method involves the removal of the 10β-methyl group by a regioselective β-scission of alkoxyl radicals. Cholesterol was transformed into two marine natural products, 19-nor-5α-cholestan-3β-ol and 19-norcholest-4-en-3-one, and into 19-norcholesta-1,3,5(10)-trien-3-ol. Transformations of 3β-hydroxyandrost-5-en-17-one into 19-nortestosterone, estrone, and the related estranes are also described.This publication has 38 references indexed in Scilit:
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