Literature DB >> 19787137

Enantio- and stereoselective route to the phoslactomycin family of antibiotics: formal synthesis of (+)-fostriecin and (+)-phoslactomycin B.

Shaheen M Sarkar1, Everlyne N Wanzala, Setsuya Shibahara, Keisuke Takahashi, Jun Ishihara, Susumi Hatakeyama.   

Abstract

A general methodology applicable for the synthesis of the phoslactomycin family of antibiotics, potent and selective protein phosphatase inhibitors, has been developed starting from a beta-isocupreidine-catalyzed asymmetric Baylis-Hillman reaction of 3-(4-methoxybenzyloxy)propanal with hexafluoroisopropyl acrylate, and thereby formal syntheses of (+)-fostriecin and (+)-phoslactomycin B have been accomplished.

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Year:  2009        PMID: 19787137     DOI: 10.1039/b912267b

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  7 in total

Review 1.  Synthetic Strategies Employed for the Construction of Fostriecin and Related Natural Products.

Authors:  Barry M Trost; Joshua D Knopf; Cheyenne S Brindle
Journal:  Chem Rev       Date:  2016-12-08       Impact factor: 60.622

2.  Total synthesis of fostriecin: via a regio- and stereoselective polyene hydration, oxidation, and hydroboration sequence.

Authors:  Dong Gao; George A O'Doherty
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

Review 3.  De novo synthesis of natural products via the asymmetric hydration of polyenes.

Authors:  Yanping Wang; Yalan Xing; Qi Zhang; George A O'Doherty
Journal:  Chem Commun (Camb)       Date:  2011-05-11       Impact factor: 6.222

4.  Total synthesis and evaluation of phostriecin and key structural analogues.

Authors:  Christopher P Burke; Mark R Swingle; Richard E Honkanen; Dale L Boger
Journal:  J Org Chem       Date:  2010-07-29       Impact factor: 4.354

5.  Total synthesis, assignment of the relative and absolute stereochemistry, and structural reassignment of phostriecin (aka Sultriecin).

Authors:  Christopher P Burke; Nadia Haq; Dale L Boger
Journal:  J Am Chem Soc       Date:  2010-02-24       Impact factor: 15.419

6.  A Highly Convergent Total Synthesis of Leustroducsin B.

Authors:  Barry M Trost; Berenger Biannic; Cheyenne S Brindle; B Michael O'Keefe; Thomas J Hunter; Ming-Yu Ngai
Journal:  J Am Chem Soc       Date:  2015-09-01       Impact factor: 15.419

7.  Preparation of an advanced intermediate for the synthesis of leustroducsins and phoslactomycins by heterocycloaddition.

Authors:  Anaïs Rousseau; Guillaume Vincent; Cyrille Kouklovsky
Journal:  Beilstein J Org Chem       Date:  2022-10-04       Impact factor: 2.544

  7 in total

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