First synthesis of ent-desmosterol and its conversion to ent-deuterocholesterol

Emily J. Westover; Douglas F. Covey

doi:10.1016/S0039-128X(02)00174-5

First synthesis of ent-desmosterol and its conversion to ent-deuterocholesterol

Emily J. Westover, Douglas F. Covey

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28 Scopus citations

Abstract

We report the first synthesis of the unnatural enantiomer of desmosterol (ent-desmosterol). The sterol nucleus was constructed enantiospecifically, followed by stepwise addition of the side chain. Beginning with ent-androst-4-ene-3,17-dione, ent-desmosterol was synthesized in 13 steps and 20% yield. Protected ent-desmosterol was subjected to catalytic deuteration to afford ent-deuterocholesterol. Ent-desmosterol and ent-deuterocholesterol will be used to study the importance of sterol absolute configuration for sterol-lipid interactions in biophysical studies and in biological systems.

Original language	English
Pages (from-to)	159-166
Number of pages	8
Journal	Steroids
Volume	68
Issue number	2
DOIs	https://doi.org/10.1016/S0039-128X(02)00174-5
State	Published - Feb 1 2003

Keywords

Enantiomers
Ent-cholesterol
Ent-desmosterol
Ent-deuterocholesterol
Sterols
Synthesis

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10.1016/S0039-128X(02)00174-5

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title = "First synthesis of ent-desmosterol and its conversion to ent-deuterocholesterol",

abstract = "We report the first synthesis of the unnatural enantiomer of desmosterol (ent-desmosterol). The sterol nucleus was constructed enantiospecifically, followed by stepwise addition of the side chain. Beginning with ent-androst-4-ene-3,17-dione, ent-desmosterol was synthesized in 13 steps and 20% yield. Protected ent-desmosterol was subjected to catalytic deuteration to afford ent-deuterocholesterol. Ent-desmosterol and ent-deuterocholesterol will be used to study the importance of sterol absolute configuration for sterol-lipid interactions in biophysical studies and in biological systems.",

keywords = "Enantiomers, Ent-cholesterol, Ent-desmosterol, Ent-deuterocholesterol, Sterols, Synthesis",

author = "Westover, {Emily J.} and Covey, {Douglas F.}",

note = "Funding Information: The authors gratefully acknowledge Gregory DeKoster for assistance in preparation of Fig. 2 and funding from: NIH GM47969 (DFC) and the Lucille P. Markey Predoctoral Fellowship and Cardiovascular Research Training Grant NIH 55935 (EJW).",

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doi = "10.1016/S0039-128X(02)00174-5",

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T1 - First synthesis of ent-desmosterol and its conversion to ent-deuterocholesterol

AU - Westover, Emily J.

AU - Covey, Douglas F.

N1 - Funding Information: The authors gratefully acknowledge Gregory DeKoster for assistance in preparation of Fig. 2 and funding from: NIH GM47969 (DFC) and the Lucille P. Markey Predoctoral Fellowship and Cardiovascular Research Training Grant NIH 55935 (EJW).

PY - 2003/2/1

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N2 - We report the first synthesis of the unnatural enantiomer of desmosterol (ent-desmosterol). The sterol nucleus was constructed enantiospecifically, followed by stepwise addition of the side chain. Beginning with ent-androst-4-ene-3,17-dione, ent-desmosterol was synthesized in 13 steps and 20% yield. Protected ent-desmosterol was subjected to catalytic deuteration to afford ent-deuterocholesterol. Ent-desmosterol and ent-deuterocholesterol will be used to study the importance of sterol absolute configuration for sterol-lipid interactions in biophysical studies and in biological systems.

AB - We report the first synthesis of the unnatural enantiomer of desmosterol (ent-desmosterol). The sterol nucleus was constructed enantiospecifically, followed by stepwise addition of the side chain. Beginning with ent-androst-4-ene-3,17-dione, ent-desmosterol was synthesized in 13 steps and 20% yield. Protected ent-desmosterol was subjected to catalytic deuteration to afford ent-deuterocholesterol. Ent-desmosterol and ent-deuterocholesterol will be used to study the importance of sterol absolute configuration for sterol-lipid interactions in biophysical studies and in biological systems.

KW - Enantiomers

KW - Ent-cholesterol

KW - Ent-desmosterol

KW - Ent-deuterocholesterol

KW - Sterols

KW - Synthesis

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U2 - 10.1016/S0039-128X(02)00174-5

DO - 10.1016/S0039-128X(02)00174-5

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C2 - 12606007

AN - SCOPUS:0037329265

SN - 0039-128X

VL - 68

SP - 159

EP - 166

JO - Steroids

JF - Steroids

IS - 2

ER -

First synthesis of ent-desmosterol and its conversion to ent-deuterocholesterol

Abstract

Keywords

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