A new method for the preparation of Ent-cholesterol from Ent- testosterone

A. Sampath Kumar; Douglas F. Covey

doi:10.1016/S0040-4039(98)02588-X

A new method for the preparation of Ent-cholesterol from Ent- testosterone

A. Sampath Kumar, Douglas F. Covey

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

16 Scopus citations

Abstract

An efficient total synthesis of the enantiomer of cholesterol is reported. The enantiomer of testosterone was prepared and converted into a C₂₁l 3-silyloxy-Δ(^5,17(20))-diene according to literature procedures. The additional five carbon atoms of the cholesterol side chain were introduced by an ene reaction. Selective hydrogenation of the resultant Δ¹⁶ double bond and removal of the 22-hydroxyl group by a mesylation and demesylation sequence gave ent-cholesterol in 9.7% overall yield from ent- testosterone.

Original language	English
Pages (from-to)	823-826
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	5
DOIs	https://doi.org/10.1016/S0040-4039(98)02588-X
State	Published - Jan 29 1999

Keywords

Enantiospecificity
Ene reactions
Stereocontrol
Steroids and Sterols

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10.1016/S0040-4039(98)02588-X

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title = "A new method for the preparation of Ent-cholesterol from Ent- testosterone",

abstract = "An efficient total synthesis of the enantiomer of cholesterol is reported. The enantiomer of testosterone was prepared and converted into a C21l 3-silyloxy-Δ(5,17(20))-diene according to literature procedures. The additional five carbon atoms of the cholesterol side chain were introduced by an ene reaction. Selective hydrogenation of the resultant Δ16 double bond and removal of the 22-hydroxyl group by a mesylation and demesylation sequence gave ent-cholesterol in 9.7% overall yield from ent- testosterone.",

keywords = "Enantiospecificity, Ene reactions, Stereocontrol, Steroids and Sterols",

author = "Kumar, {A. Sampath} and Covey, {Douglas F.}",

note = "Funding Information: Acknowledgement: This work was supported by NIH grant GM 47969.",

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doi = "10.1016/S0040-4039(98)02588-X",

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T1 - A new method for the preparation of Ent-cholesterol from Ent- testosterone

AU - Kumar, A. Sampath

AU - Covey, Douglas F.

N1 - Funding Information: Acknowledgement: This work was supported by NIH grant GM 47969.

PY - 1999/1/29

Y1 - 1999/1/29

N2 - An efficient total synthesis of the enantiomer of cholesterol is reported. The enantiomer of testosterone was prepared and converted into a C21l 3-silyloxy-Δ(5,17(20))-diene according to literature procedures. The additional five carbon atoms of the cholesterol side chain were introduced by an ene reaction. Selective hydrogenation of the resultant Δ16 double bond and removal of the 22-hydroxyl group by a mesylation and demesylation sequence gave ent-cholesterol in 9.7% overall yield from ent- testosterone.

AB - An efficient total synthesis of the enantiomer of cholesterol is reported. The enantiomer of testosterone was prepared and converted into a C21l 3-silyloxy-Δ(5,17(20))-diene according to literature procedures. The additional five carbon atoms of the cholesterol side chain were introduced by an ene reaction. Selective hydrogenation of the resultant Δ16 double bond and removal of the 22-hydroxyl group by a mesylation and demesylation sequence gave ent-cholesterol in 9.7% overall yield from ent- testosterone.

KW - Enantiospecificity

KW - Ene reactions

KW - Stereocontrol

KW - Steroids and Sterols

UR - http://www.scopus.com/inward/record.url?scp=0033613797&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(98)02588-X

DO - 10.1016/S0040-4039(98)02588-X

M3 - Article

AN - SCOPUS:0033613797

SN - 0040-4039

VL - 40

SP - 823

EP - 826

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 5

ER -

A new method for the preparation of Ent-cholesterol from Ent- testosterone

Abstract

Keywords

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