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Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate

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1988
Authors
Mihailović, Mihailo Lj.
Lorenc, Ljubinka
Dabović, Milan
Bjelaković, Mira
Article (Published version)
,
Elsevier
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Abstract
The oxidation of androst-4-ene-3β,9α,17β-triol 3,17-diacetate (2) with lead tetraacetate resulted mainly In β-fragmentation of the C(9)-C(10) bond to give a mixture of 10α- and 10β-acetoxy-Δ4-unsaturated 9,10-seco-steroidal ketones (3a and 3b) as the minor components (in ~7% yield) and the rearranged 4β-acetoxy-Δ5(10) -unsaturated 9,10-seco-9-ketone (4) as the major product (in 61% yield). Unexpectedly, when the same substrate (2) was subjected to the mercuric oxide - iodine oxidation, it underwent predominantly α-epoxidation of the olefinic double bond to produce the 4α,5α-epoxy derivative (5) (in 58% yield). © 1988.
Source:
Tetrahedron, 1988, 44, 19, 6201-6206
Projects:
  • Serbian Academy of Sciences and Arts
  • Serbian Republic Research Fund

DOI: 10.1016/S0040-4020(01)89810-0

ISSN: 0040-4020

Scopus: 2-s2.0-0344746322
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/2699
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