Literature DB >> 20228884

Scalable and efficient synthesis of the mycolactone core.

Katrina L Jackson1, Wenju Li, Chi-Li Chen, Yoshito Kishi.   

Abstract

A highly efficient, scalable, and stereoselective synthesis of the mycolactone core is reported. The synthesis consists of 14 longest linear steps, with 19% overall yield.

Entities:  

Year:  2010        PMID： 20228884      PMCID： PMC2835472          DOI： 10.1016/j.tet.2010.02.010

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  36 in total

1.  Stereochemistry of the core structure of the mycolactones.

Authors:  A B Benowitz; S Fidanze; P L Small; Y Kishi
Journal:  J Am Chem Soc       Date:  2001-05-30       Impact factor: 15.419

2.  Complete structure of the mycolactones.

Authors:  S Fidanze; F Song; M Szlosek-Pinaud; P L Small; Y Kishi
Journal:  J Am Chem Soc       Date:  2001-10-17       Impact factor: 15.419

3.  Synthesis of the mycolactone core by ring-closing metathesis.

Authors:  Matthew D Alexander; Shaun D Fontaine; James J La Clair; Antonio G Dipasquale; Arnold L Rheingold; Michael D Burkart
Journal:  Chem Commun (Camb)       Date:  2006-09-21       Impact factor: 6.222

4.  Total Synthesis of Mycolactones A and B.

Authors:  Fengbin Song; Steve Fidanze; Andrew B Benowitz; Yoshito Kishi
Journal:  Tetrahedron       Date:  2007-06-25       Impact factor: 2.457

5.  Total synthesis and stereochemistry of mycolactone F.

Authors:  Han-Je Kim; Yoshito Kishi
Journal:  J Am Chem Soc       Date:  2008-01-19       Impact factor: 15.419

6.  Mycolactone: a polyketide toxin from Mycobacterium ulcerans required for virulence.

Authors:  K M George; D Chatterjee; G Gunawardana; D Welty; J Hayman; R Lee; P L Small
Journal:  Science       Date:  1999-02-05       Impact factor: 47.728

Review 7.  Mycobacterium ulcerans disease.

Authors:  Tjip S van der Werf; Ymkje Stienstra; R Christian Johnson; Richard Phillips; Ohene Adjei; Bernhard Fleischer; Mark H Wansbrough-Jones; Paul D R Johnson; Françoise Portaels; Winette T A van der Graaf; Kingsley Asiedu
Journal:  Bull World Health Organ       Date:  2005-11-10       Impact factor: 9.408

Review 8.  Buruli ulcer: reductive evolution enhances pathogenicity of Mycobacterium ulcerans.

Authors:  Caroline Demangel; Timothy P Stinear; Stewart T Cole
Journal:  Nat Rev Microbiol       Date:  2009-01       Impact factor: 60.633

9.  Synthesis and structure of mycolactone E isolated from frog mycobacterium.

Authors:  Sylvain Aubry; Richard E Lee; Engy A Mahrous; Pam L C Small; Dia Beachboard; Yoshito Kishi
Journal:  Org Lett       Date:  2008-12-04       Impact factor: 6.005

10.  Selective suppression of dendritic cell functions by Mycobacterium ulcerans toxin mycolactone.

Authors:  Emmanuelle Coutanceau; Jeremie Decalf; Angelo Martino; Aurélie Babon; Nathalie Winter; Stewart T Cole; Matthew L Albert; Caroline Demangel
Journal:  J Exp Med       Date:  2007-05-21       Impact factor: 14.307
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  4 in total

1.  Highly stereoselective total synthesis of fully hydroxy-protected mycolactones A and B and their stereoisomerization upon deprotection.

Authors:  Guangwei Wang; Ning Yin; Ei-ichi Negishi
Journal:  Chemistry       Date:  2011-03-15       Impact factor: 5.236

2.  Chemistry of mycolactones, the causative toxins of Buruli ulcer.

Authors:  Yoshito Kishi
Journal:  Proc Natl Acad Sci U S A       Date:  2011-03-07       Impact factor: 11.205

Review 3.  The chemistry and biology of mycolactones.

Authors:  Matthias Gehringer; Karl-Heinz Altmann
Journal:  Beilstein J Org Chem       Date:  2017-08-11       Impact factor: 2.883

4.  Structure-activity relationship studies on the macrolide exotoxin mycolactone of Mycobacterium ulcerans.

Authors:  Nicole Scherr; Philipp Gersbach; Jean-Pierre Dangy; Claudio Bomio; Jun Li; Karl-Heinz Altmann; Gerd Pluschke
Journal:  PLoS Negl Trop Dis       Date:  2013-03-28
  4 in total

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