A convenient access to 16-methylene and 16β-methyl corticosteroids by a novel transformation of geminal bis(phenylsulphinyl) intermediates

Jean Boivin; Christine Chauvet; Samir Z. Zard

doi:10.1016/S0040-4039(00)61232-7

A convenient access to 16-methylene and 16β-methyl corticosteroids by a novel transformation of geminal bis(phenylsulphinyl) intermediates

Jean Boivin
, Christine Chauvet
, Samir Z. Zard

Laboratoire de Synthèse Organique

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

Abstract

16α-Bis(phenylsulphinyl) methyl pregnane derivative 7 gives, by a series of eliminations and rearrangements, the corresponding 16-methylene intermediate 4 on heating in the presence of triphenylphosphine. Regio- and stereoselective hydrogenation of the latter using Wilkinson's catalyst furnishes 16β-methyl corticosteroids 5.

Original language	English
Pages (from-to)	4913-4916
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	34
DOIs	https://doi.org/10.1016/S0040-4039(00)61232-7
Publication status	Published - 18 Aug 1992
Externally published	Yes

Access to Document

10.1016/S0040-4039(00)61232-7

Cite this

@article{56b9af2dbf254fd09aec92685903de0b,

title = "A convenient access to 16-methylene and 16β-methyl corticosteroids by a novel transformation of geminal bis(phenylsulphinyl) intermediates",

abstract = "16α-Bis(phenylsulphinyl) methyl pregnane derivative 7 gives, by a series of eliminations and rearrangements, the corresponding 16-methylene intermediate 4 on heating in the presence of triphenylphosphine. Regio- and stereoselective hydrogenation of the latter using Wilkinson's catalyst furnishes 16β-methyl corticosteroids 5.",

author = "Jean Boivin and Christine Chauvet and Zard, \{Samir Z.\}",

year = "1992",

month = aug,

day = "18",

doi = "10.1016/S0040-4039(00)61232-7",

language = "English",

volume = "33",

pages = "4913--4916",

journal = "Tetrahedron Letters",

issn = "0040-4039",

number = "34",

}

TY - JOUR

T1 - A convenient access to 16-methylene and 16β-methyl corticosteroids by a novel transformation of geminal bis(phenylsulphinyl) intermediates

AU - Boivin, Jean

AU - Chauvet, Christine

AU - Zard, Samir Z.

PY - 1992/8/18

Y1 - 1992/8/18

N2 - 16α-Bis(phenylsulphinyl) methyl pregnane derivative 7 gives, by a series of eliminations and rearrangements, the corresponding 16-methylene intermediate 4 on heating in the presence of triphenylphosphine. Regio- and stereoselective hydrogenation of the latter using Wilkinson's catalyst furnishes 16β-methyl corticosteroids 5.

AB - 16α-Bis(phenylsulphinyl) methyl pregnane derivative 7 gives, by a series of eliminations and rearrangements, the corresponding 16-methylene intermediate 4 on heating in the presence of triphenylphosphine. Regio- and stereoselective hydrogenation of the latter using Wilkinson's catalyst furnishes 16β-methyl corticosteroids 5.

UR - https://www.scopus.com/pages/publications/0026674357

U2 - 10.1016/S0040-4039(00)61232-7

DO - 10.1016/S0040-4039(00)61232-7

M3 - Article

AN - SCOPUS:0026674357

SN - 0040-4039

VL - 33

SP - 4913

EP - 4916

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 34

ER -

A convenient access to 16-methylene and 16β-methyl corticosteroids by a novel transformation of geminal bis(phenylsulphinyl) intermediates

Abstract

Access to Document

Other files and links

Fingerprint

Cite this