Synthesis of side-chain oxysterols and their enantiomers through cross-metathesis reactions of Δ22 steroids

David P. Brownholland; Douglas F. Covey

doi:10.1016/j.steroids.2017.03.002

Synthesis of side-chain oxysterols and their enantiomers through cross-metathesis reactions of Δ²² steroids

David P. Brownholland, Douglas F. Covey

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

3 Scopus citations

Abstract

A synthetic route that utilizes a cross-metathesis reaction with Δ²² steroids has been developed to prepare sterols with varying C-27 side-chains. Natural sterols containing hydroxyl groups at the 25 and (25R)-26 positions were prepared. Enantiomers of cholesterol and (3β,25R)-26-hydroxycholesterol (27-hydroxycholesterol) trideuterated at C-19 were prepared for future biological studies.

Original language	English
Pages (from-to)	22-31
Number of pages	10
Journal	Steroids
Volume	121
DOIs	https://doi.org/10.1016/j.steroids.2017.03.002
State	Published - 2017

Keywords

Cross-metathesis
Grubbs catalyst
Ruthenium catalyst
Side-chain oxysterols
ent-steroids
Δ-steroids

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10.1016/j.steroids.2017.03.002

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title = "Synthesis of side-chain oxysterols and their enantiomers through cross-metathesis reactions of Δ22 steroids",

abstract = "A synthetic route that utilizes a cross-metathesis reaction with Δ22 steroids has been developed to prepare sterols with varying C-27 side-chains. Natural sterols containing hydroxyl groups at the 25 and (25R)-26 positions were prepared. Enantiomers of cholesterol and (3β,25R)-26-hydroxycholesterol (27-hydroxycholesterol) trideuterated at C-19 were prepared for future biological studies.",

keywords = "Cross-metathesis, Grubbs catalyst, Ruthenium catalyst, Side-chain oxysterols, ent-steroids, Δ-steroids",

author = "Brownholland, {David P.} and Covey, {Douglas F.}",

note = "Publisher Copyright: {\textcopyright} 2017 Elsevier Inc.",

year = "2017",

doi = "10.1016/j.steroids.2017.03.002",

language = "English",

volume = "121",

pages = "22--31",

journal = "Steroids",

issn = "0039-128X",

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T1 - Synthesis of side-chain oxysterols and their enantiomers through cross-metathesis reactions of Δ22 steroids

AU - Brownholland, David P.

AU - Covey, Douglas F.

PY - 2017

Y1 - 2017

N2 - A synthetic route that utilizes a cross-metathesis reaction with Δ22 steroids has been developed to prepare sterols with varying C-27 side-chains. Natural sterols containing hydroxyl groups at the 25 and (25R)-26 positions were prepared. Enantiomers of cholesterol and (3β,25R)-26-hydroxycholesterol (27-hydroxycholesterol) trideuterated at C-19 were prepared for future biological studies.

AB - A synthetic route that utilizes a cross-metathesis reaction with Δ22 steroids has been developed to prepare sterols with varying C-27 side-chains. Natural sterols containing hydroxyl groups at the 25 and (25R)-26 positions were prepared. Enantiomers of cholesterol and (3β,25R)-26-hydroxycholesterol (27-hydroxycholesterol) trideuterated at C-19 were prepared for future biological studies.

KW - Cross-metathesis

KW - Grubbs catalyst

KW - Ruthenium catalyst

KW - Side-chain oxysterols

KW - ent-steroids

KW - Δ-steroids

UR - http://www.scopus.com/inward/record.url?scp=85015744830&partnerID=8YFLogxK

U2 - 10.1016/j.steroids.2017.03.002

DO - 10.1016/j.steroids.2017.03.002

M3 - Article

C2 - 28300584

AN - SCOPUS:85015744830

SN - 0039-128X

VL - 121

SP - 22

EP - 31

JO - Steroids

JF - Steroids

ER -

Synthesis of side-chain oxysterols and their enantiomers through cross-metathesis reactions of Δ²² steroids

Abstract

Keywords

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