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

Mihailović, Milhailo Lj.; Lorenc, Ljubinka; Dabović, Milan; Bjelaković, Mira

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

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1988

Authors

Mihailović, Milhailo 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

Funding / 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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	4

TY  - JOUR
AU  - Mihailović, Milhailo Lj.
AU  - Lorenc, Ljubinka
AU  - Dabović, Milan
AU  - Bjelaković, Mira
PY  - 1988
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2699
AB  - 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.
T2  - Tetrahedron
T1  - Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate
VL  - 44
IS  - 19
SP  - 6201
EP  - 6206
DO  - 10.1016/S0040-4020(01)89810-0
ER  -

@article{
author = "Mihailović, Milhailo Lj. and Lorenc, Ljubinka and Dabović, Milan and Bjelaković, Mira",
year = "1988",
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.",
journal = "Tetrahedron",
title = "Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate",
volume = "44",
number = "19",
pages = "6201-6206",
doi = "10.1016/S0040-4020(01)89810-0"
}

Mihailović, M. Lj., Lorenc, L., Dabović, M.,& Bjelaković, M.. (1988). Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate. in Tetrahedron, 44(19), 6201-6206.
https://doi.org/10.1016/S0040-4020(01)89810-0

Mihailović ML, Lorenc L, Dabović M, Bjelaković M. Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate. in Tetrahedron. 1988;44(19):6201-6206.
doi:10.1016/S0040-4020(01)89810-0 .

Mihailović, Milhailo Lj., Lorenc, Ljubinka, Dabović, Milan, Bjelaković, Mira, "Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate" in Tetrahedron, 44, no. 19 (1988):6201-6206,
https://doi.org/10.1016/S0040-4020(01)89810-0 . .