Isolation and structure elucidation of new radical oxidation products of 5-hydroxy steroids

V.A. Khripach; V.N. Zhabinskii; A.I. Kuchto; Y.Y. Zhiburtovich; A.S. Lyakhov; A.A. Govorova; M.B. Groen; J. van der Louw; Æ. de Groot

doi:10.1016/j.steroids.2006.01.008

Isolation and structure elucidation of new radical oxidation products of 5-hydroxy steroids

V.A. Khripach
, V.N. Zhabinskii
, A.I. Kuchto
, Y.Y. Zhiburtovich
, A.S. Lyakhov
, A.A. Govorova
, M.B. Groen
, J. van der Louw
, Æ. de Groot

Research output: Contribution to journal › Article › Academic › peer-review

5 Citations (Scopus)

Abstract

Three new products have been isolated from the lead-tetraacetate version of the hypoiodite oxidation of 3 beta,17 beta-diacetoxy-5-hydroxy-5 alpha-androstane. Along with the expected 1(10)unsaturated 5,10-seco steroidal 5-ketones, the fragmentation reaction gave two epimeric C-4 iodides. Their structural assignment was based on X-ray data of one of them ((4R,10S)-4iodo-3 beta,17 beta-diacetoxy-5,10-secoandrostan-5-one). The third new product was found to be the 5 beta,6 beta-epoxide resulting from the dehydration of the tertiary alcohol followed by epoxidation of the intermediate Delta(5)-olefin.

Original language	English
Pages (from-to)	504-509
Journal	Steroids
Volume	71
Issue number	6
DOIs	https://doi.org/10.1016/j.steroids.2006.01.008
Publication status	Published - 2006

Keywords

medium-sized ring
10-membered ring
fragmentation
reactivity
13,14-seco-steroids
conformations
secosteroids
epoxidation

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10.1016/j.steroids.2006.01.008

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@article{65b97c2c674d4e6192d6c0e83586005e,

title = "Isolation and structure elucidation of new radical oxidation products of 5-hydroxy steroids",

abstract = "Three new products have been isolated from the lead-tetraacetate version of the hypoiodite oxidation of 3 beta,17 beta-diacetoxy-5-hydroxy-5 alpha-androstane. Along with the expected 1(10)unsaturated 5,10-seco steroidal 5-ketones, the fragmentation reaction gave two epimeric C-4 iodides. Their structural assignment was based on X-ray data of one of them ((4R,10S)-4iodo-3 beta,17 beta-diacetoxy-5,10-secoandrostan-5-one). The third new product was found to be the 5 beta,6 beta-epoxide resulting from the dehydration of the tertiary alcohol followed by epoxidation of the intermediate Delta(5)-olefin.",

keywords = "medium-sized ring, 10-membered ring, fragmentation, reactivity, 13,14-seco-steroids, conformations, secosteroids, epoxidation",

author = "V.A. Khripach and V.N. Zhabinskii and A.I. Kuchto and Y.Y. Zhiburtovich and A.S. Lyakhov and A.A. Govorova and M.B. Groen and \{van der Louw\}, J. and \{de Groot\}, {\AE}.",

note = "ISI Document Delivery No.: 045CQ Times Cited: 1 Cited Reference Count: 19",

year = "2006",

doi = "10.1016/j.steroids.2006.01.008",

language = "English",

volume = "71",

pages = "504--509",

journal = "Steroids",

issn = "0039-128X",

publisher = "Elsevier",

number = "6",

}

TY - JOUR

T1 - Isolation and structure elucidation of new radical oxidation products of 5-hydroxy steroids

AU - Khripach, V.A.

AU - Zhabinskii, V.N.

AU - Kuchto, A.I.

AU - Zhiburtovich, Y.Y.

AU - Lyakhov, A.S.

AU - Govorova, A.A.

AU - Groen, M.B.

AU - van der Louw, J.

AU - de Groot, Æ.

N1 - ISI Document Delivery No.: 045CQ Times Cited: 1 Cited Reference Count: 19

PY - 2006

Y1 - 2006

N2 - Three new products have been isolated from the lead-tetraacetate version of the hypoiodite oxidation of 3 beta,17 beta-diacetoxy-5-hydroxy-5 alpha-androstane. Along with the expected 1(10)unsaturated 5,10-seco steroidal 5-ketones, the fragmentation reaction gave two epimeric C-4 iodides. Their structural assignment was based on X-ray data of one of them ((4R,10S)-4iodo-3 beta,17 beta-diacetoxy-5,10-secoandrostan-5-one). The third new product was found to be the 5 beta,6 beta-epoxide resulting from the dehydration of the tertiary alcohol followed by epoxidation of the intermediate Delta(5)-olefin.

AB - Three new products have been isolated from the lead-tetraacetate version of the hypoiodite oxidation of 3 beta,17 beta-diacetoxy-5-hydroxy-5 alpha-androstane. Along with the expected 1(10)unsaturated 5,10-seco steroidal 5-ketones, the fragmentation reaction gave two epimeric C-4 iodides. Their structural assignment was based on X-ray data of one of them ((4R,10S)-4iodo-3 beta,17 beta-diacetoxy-5,10-secoandrostan-5-one). The third new product was found to be the 5 beta,6 beta-epoxide resulting from the dehydration of the tertiary alcohol followed by epoxidation of the intermediate Delta(5)-olefin.

KW - medium-sized ring

KW - 10-membered ring

KW - fragmentation

KW - reactivity

KW - 13,14-seco-steroids

KW - conformations

KW - secosteroids

KW - epoxidation

U2 - 10.1016/j.steroids.2006.01.008

DO - 10.1016/j.steroids.2006.01.008

M3 - Article

SN - 0039-128X

VL - 71

SP - 504

EP - 509

JO - Steroids

JF - Steroids

IS - 6

ER -

Isolation and structure elucidation of new radical oxidation products of 5-hydroxy steroids

Abstract

Keywords

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