Literature DB >> 24079664

Total synthesis of epothilone D: the nerol/macroaldolization approach.

Ludger A Wessjohann1, Günther O Scheid, Uwe Eichelberger, Sumaira Umbreen.   

Abstract

A highly convergent and stereocontrolled synthesis of epothilone D (4) is reported. Key features are a cheap and Z-selective synthesis of the northern half based on nerol and acetoacetate and chromium(II)-mediated Reformatsky reactions as a powerful tool for chemoselective asymmetric carbon-carbon bond formations, including an unusual stereospecific macroaldolization.

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Year:  2013        PMID: 24079664     DOI: 10.1021/jo401355r

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


  4 in total

1.  Stereoselective Synthesis of Homoneryl and Homogeranyl Triazole Bisphosphonates.

Authors:  Robert A Matthiesen; Veronica S Wills; Joseph I Metzger; Sarah A Holstein; David F Wiemer
Journal:  J Org Chem       Date:  2016-09-20       Impact factor: 4.354

2.  Prof. Ludger Wessjohann: A Lifelong Career Dedicated to a Remarkable Service in "Natural Products Sciences".

Authors:  Hidayat Hussain
Journal:  Int J Mol Sci       Date:  2022-05-13       Impact factor: 6.208

3.  A Highly Stereoselective, Efficient, and Scalable Synthesis of the C(1)-C(9) Fragment of the Epothilones.

Authors:  Corinne N Foley; James L Leighton
Journal:  Org Lett       Date:  2015-11-12       Impact factor: 6.005

Review 4.  Recent developments in the asymmetric Reformatsky-type reaction.

Authors:  Hélène Pellissier
Journal:  Beilstein J Org Chem       Date:  2018-02-02       Impact factor: 2.883

  4 in total

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