Literature DB >> 15609966

Total syntheses of epothilones B and d.

Jae-Chul Jung1, Rajashaker Kache, Kimberly K Vines, Yan-Song Zheng, Panicker Bijoy, Muralikrishna Valluri, Mitchell A Avery.   

Abstract

A convergent, total synthesis of epothilones B (2) and D (4) is described. The key steps are Normant coupling to establish the desired (Z)-stereochemistry at C12-C13, Wadsworth-Emmons olefination of methyl ketone 28 with the phosphonate ester 8, diastereoselective aldol condensation of aldehyde 5 with the enolate of keto acid derivatives to form the C6-C7 bond, selective deprotection of acid 52, and macrolactonization.

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Year:  2004        PMID: 15609966     DOI: 10.1021/jo048742o

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


  3 in total

1.  Total synthesis of epothilones B and D: stannane equivalents for beta-keto ester dianions.

Authors:  Gary E Keck; Robert L Giles; Victor J Cee; Carrie A Wager; Tao Yu; Matthew B Kraft
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

2.  Stereoselective Radical C-H Alkylation with Acceptor/Acceptor-Substituted Diazo Reagents via Co(II)-Based Metalloradical Catalysis.

Authors:  Xin Cui; Xue Xu; Li-Mei Jin; Lukasz Wojtas; X Peter Zhang
Journal:  Chem Sci       Date:  2015-02       Impact factor: 9.825

3.  Epothilones Suppress Neointimal Thickening in the Rat Carotid Balloon-Injury Model by Inducing Vascular Smooth Muscle Cell Apoptosis through p53-Dependent Signaling Pathway.

Authors:  Dong Ju Son; Jae Chul Jung; Jin Tae Hong
Journal:  PLoS One       Date:  2016-05-24       Impact factor: 3.240

  3 in total

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