Literature DB >> 18336043

A concise synthesis of ent-Cholesterol.

Jitendra D Belani1, Scott D Rychnovsky.   

Abstract

ent-Cholesterol was synthesized in 16 steps from commercially available (S)-citronellol. The overall yield for the synthesis was 2.0%. This route is amenable to gram-scale preparation of ent-cholesterol. Isotopic incorporation near the end of the synthesis was achieved using labeled methyl iodide. This synthesis is the most practical to date and will make ent-cholesterol more readily available to use as a probe of the function and metabolism of cholesterol.

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Year:  2008        PMID： 18336043      PMCID： PMC2729551          DOI： 10.1021/jo702694g

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  9 in total

1.  Synthesis of (-)-astrogorgiadiol.

Authors:  D F Taber; S C Malcolm
Journal:  J Org Chem       Date:  2001-02-09       Impact factor: 4.354

2.  Enantiospecificity of cholesterol function in vivo.

Authors:  C M Crowder; E J Westover; A S Kumar; R E Ostlund; D F Covey
Journal:  J Biol Chem       Date:  2001-10-11       Impact factor: 5.157

3.  Total syntheses of optically active 19-norsteroids. (+)-Estr-4-ene-3,17-dione and (+)13 beta-ethylgon-4-ene-3,17-dione.

Authors:  R A Micheli; Z G Hajos; N Cohen; D R Parrish; L A Portland; W Sciamanna; M A Scott; P A Wehrli
Journal:  J Org Chem       Date:  1975-03-21       Impact factor: 4.354

4.  Stereocontrolled total synthesis of 19-nor steroids.

Authors:  Z G Hajos; D R Parrish
Journal:  J Org Chem       Date:  1973-09-21       Impact factor: 4.354

5.  Role of chirality in peptide-induced formation of cholesterol-rich domains.

Authors:  Richard M Epand; Scott D Rychnovsky; Jitendra D Belani; Raquel F Epand
Journal:  Biochem J       Date:  2005-09-01       Impact factor: 3.857

6.  Dual roles for cholesterol in mammalian cells.

Authors:  Fang Xu; Scott D Rychnovsky; Jitendra D Belani; Helen H Hobbs; Jonathan C Cohen; Robert B Rawson
Journal:  Proc Natl Acad Sci U S A       Date:  2005-09-30       Impact factor: 11.205

7.  Effects of cholesterol and enantiomeric cholesterol on P-glycoprotein localization and function in low-density membrane domains.

Authors:  G D Luker; C M Pica; A S Kumar; D F Covey; D Piwnica-Worms
Journal:  Biochemistry       Date:  2000-07-04       Impact factor: 3.162

8.  Total synthesis of ent-cholesterol via a steroid C,D-ring side-chain synthon.

Authors:  Xin Jiang; Douglas F Covey
Journal:  J Org Chem       Date:  2002-07-12       Impact factor: 4.354

9.  Cholesterol depletion results in site-specific increases in epidermal growth factor receptor phosphorylation due to membrane level effects. Studies with cholesterol enantiomers.

Authors:  Emily J Westover; Douglas F Covey; Howard L Brockman; Rhoderick E Brown; Linda J Pike
Journal:  J Biol Chem       Date:  2003-10-06       Impact factor: 5.157
  9 in total
  6 in total

1.  Hedgehog pathway modulation by multiple lipid binding sites on the smoothened effector of signal response.

Authors:  Benjamin R Myers; Navdar Sever; Yong Chun Chong; James Kim; Jitendra D Belani; Scott Rychnovsky; J Fernando Bazan; Philip A Beachy
Journal:  Dev Cell       Date:  2013-08-15       Impact factor: 12.270

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

Authors:  David P Brownholland; Douglas F Covey
Journal:  Steroids       Date:  2017-03-12       Impact factor: 2.668

3.  Distinct mechanisms underlying cholesterol protection against alcohol-induced BK channel inhibition and resulting vasoconstriction.

Authors:  Shivantika Bisen; Olga Seleverstov; Jitendra Belani; Scott Rychnovsky; Alex M Dopico; Anna N Bukiya
Journal:  Biochim Biophys Acta       Date:  2016-08-24

Review 4.  ent-Steroids: novel tools for studies of signaling pathways.

Authors:  Douglas F Covey
Journal:  Steroids       Date:  2008-12-03       Impact factor: 2.668

5.  Cholesterol through the looking glass: ability of its enantiomer also to elicit homeostatic responses.

Authors:  Ika Kristiana; Winnie Luu; Julian Stevenson; Sian Cartland; Wendy Jessup; Jitendra D Belani; Scott D Rychnovsky; Andrew J Brown
Journal:  J Biol Chem       Date:  2012-08-06       Impact factor: 5.157

6.  Specificity of cholesterol and analogs to modulate BK channels points to direct sterol-channel protein interactions.

Authors:  Anna N Bukiya; Jitendra D Belani; Scott Rychnovsky; Alex M Dopico
Journal:  J Gen Physiol       Date:  2010-12-13       Impact factor: 4.086
  6 in total

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