Literature DB >> 28300584

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

David P Brownholland1, Douglas F Covey2.   

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.
Copyright © 2017 Elsevier Inc. All rights reserved.

Entities:  

Keywords:  Cross-metathesis; Grubbs catalyst; Ruthenium catalyst; Side-chain oxysterols; ent-steroids; Δ(22)-steroids

Mesh：

Substances：

Year:  2017        PMID： 28300584      PMCID： PMC5398201          DOI： 10.1016/j.steroids.2017.03.002

Source DB:  PubMed          Journal:  Steroids        ISSN： 0039-128X            Impact factor:   2.668


  26 in total

1.  Clemmensen reduction of diosgenin and kryptogenin: synthesis of [16,16,22,22,23,23-(2)H(6)]-(25R)-26-hydroxycholesterol.

Authors:  Laura Alessandrini; Pierangela Ciuffreda; Enzo Santaniello; Giancarlo Terraneo
Journal:  Steroids       Date:  2004-12       Impact factor: 2.668

Review 2.  Are side-chain oxidized oxysterols regulators also in vivo?

Authors:  Ingemar Björkhem
Journal:  J Lipid Res       Date:  2008-10-23       Impact factor: 5.922

3.  Synthesis of (25R)-26-hydroxycholesterol.

Authors:  John R Williams; Deping Chai; Dominic Wright
Journal:  Steroids       Date:  2002-12       Impact factor: 2.668

4.  Synthesis, characterization, and receptor interaction profiles of enantiomeric bile acids.

Authors:  Bryson W Katona; Carolyn L Cummins; Andrew D Ferguson; Tingting Li; Daniel R Schmidt; David J Mangelsdorf; Douglas F Covey
Journal:  J Med Chem       Date:  2007-10-27       Impact factor: 7.446

5.  A concise synthesis of ent-Cholesterol.

Authors:  Jitendra D Belani; Scott D Rychnovsky
Journal:  J Org Chem       Date:  2008-03-13       Impact factor: 4.354

6.  Synthesis of 19-Trideuterated ent-Testosterone and the GABA(A) Receptor Potentiators ent-Androsterone and ent-Etiocholanolone.

Authors:  Shirisha Komarapuri; Kathiresan Krishnan; Douglas F Covey
Journal:  J Labelled Comp Radiopharm       Date:  2008-11       Impact factor: 1.921

7.  Differential effects of 24-hydroxycholesterol and 27-hydroxycholesterol on tyrosine hydroxylase and alpha-synuclein in human neuroblastoma SH-SY5Y cells.

Authors:  Jaya Prasanthi Rantham Prabhakara; Gwen Feist; Sarah Thomasson; Alex Thompson; Eric Schommer; Othman Ghribi
Journal:  J Neurochem       Date:  2008-11-05       Impact factor: 5.372

Review 8.  Oxysterol signaling links cholesterol metabolism and inflammation via the liver X receptor in macrophages.

Authors:  Dániel Töröcsik; Attila Szanto; László Nagy
Journal:  Mol Aspects Med       Date:  2009-02-25

9.  Stereoselective synthesis of the hormonally active (25S)-delta7-dafachronic acid, (25S)-Delta4-dafachronic acid, (25S)-dafachronic acid, and (25S)-cholestenoic acid.

Authors:  René Martin; Frank Däbritz; Eugeni V Entchev; Teymuras V Kurzchalia; Hans-Joachim Knölker
Journal:  Org Biomol Chem       Date:  2008-10-17       Impact factor: 3.876

Review 10.  Enzymes in the conversion of cholesterol into bile acids.

Authors:  Maria Norlin; Kjell Wikvall
Journal:  Curr Mol Med       Date:  2007-03       Impact factor: 2.222
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