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Synthesis of side-chain oxysterols and their enantiomers through cross-metathesis reactions of ?22 steroids.

ABSTRACT: A synthetic route that utilizes a cross-metathesis reaction with ?22 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 (3?,25R)-26-hydroxycholesterol (27-hydroxycholesterol) trideuterated at C-19 were prepared for future biological studies.

SUBMITTER: Brownholland DP

PROVIDER: S-EPMC5398201 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

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Synthesis of side-chain oxysterols and their enantiomers through cross-metathesis reactions of Δ<sup>22</sup> steroids.

Brownholland David P DP Covey Douglas F DF

Steroids 20170312

A synthetic route that utilizes a cross-metathesis reaction with Δ<sup>22</sup> 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. ...[more]

PMID: 28300584

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