Literature DB >> 19492384

Decarboxylative Grob-type fragmentations in the synthesis of trisubstituted Z olefins: application to peloruside A, discodermolide, and epothilone D.

Kathrin Prantz1, Johann Mulzer.   

Abstract

Discriminating elimination: A new method for the synthesis of methyl-branched trisubstituted Z olefins, a structural motif in many polyketides with anticancer activity, relies on an (-)OH-induced decarboxylative Grob-type fragmentation (see scheme; Ms = mesyl). The starting materials are beta-mesyloxy lactones with a quaternary alpha center, which are prepared by aldol reactions in a diastereo- and enantioselective manner.

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Year:  2009        PMID： 19492384     DOI： 10.1002/anie.200901740

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  6 in total

1.  Total synthesis of peloruside A through kinetic lactonization and relay ring-closing metathesis cyclization reactions.

Authors:  Thomas R Hoye; Junha Jeon; Lucas C Kopel; Troy D Ryba; Manomi A Tennakoon; Yini Wang
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-16       Impact factor: 15.336

2.  SYNTHESIS OF (S,S)-DIISOPROPYL TARTRATE (E)-CROTYLBORONATE AND ITS REACTION WITH ALDEHYDES: (2R,3R,4R)-1,2-DIDEOXY-2-ETHENYL-4,5-O-(1-METHYLETHYLIDENE)-XYLITOL.

Authors:  Huikai Sun; William R Roush; David A Candito; Mathieu Blanchot; Mark Lautens
Journal:  Organic Synth       Date:  2011

Review 3.  Recent progress with microtubule stabilizers: new compounds, binding modes and cellular activities.

Authors:  Cristina C Rohena; Susan L Mooberry
Journal:  Nat Prod Rep       Date:  2014-03       Impact factor: 13.423

4.  Peloruside B, a potent antitumor macrolide from the New Zealand marine sponge Mycale hentscheli: isolation, structure, total synthesis, and bioactivity.

Authors:  A Jonathan Singh; Chun-Xiao Xu; Xiaoming Xu; Lyndon M West; Anja Wilmes; Ariane Chan; Ernest Hamel; John H Miller; Peter T Northcote; Arun K Ghosh
Journal:  J Org Chem       Date:  2010-01-01       Impact factor: 4.354

5.  Strobilurin biosynthesis in Basidiomycete fungi.

Authors:  Risa Nofiani; Kate de Mattos-Shipley; Karen E Lebe; Li-Chen Han; Zafar Iqbal; Andrew M Bailey; Christine L Willis; Thomas J Simpson; Russell J Cox
Journal:  Nat Commun       Date:  2018-09-26       Impact factor: 14.919

6.  Total Synthesis of (-)-Mitrephorone A Enabled by Stereoselective Nitrile Oxide Cycloaddition and Tetrasubstituted Olefin Synthesis.

Authors:  Michael Schneider; Matthieu J R Richter; Erick M Carreira
Journal:  J Am Chem Soc       Date:  2020-10-06       Impact factor: 15.419
  6 in total

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