Literature DB >> 18393518

Expedient synthesis of the tetracyclic core of ent-nakadomarin A.

Haibing Deng1, Xiaobao Yang, Zhaolong Tong, Zhong Li, Hongbin Zhai.   

Abstract

An efficient eight-step assembly of the tetracyclic core (ABCD rings) of ent-(+)-nakadomarin A, a bioactive hexacyclic marine alkaloid, has been realized with Sonogashira coupling, platinum(II)-promoted cascade cyclizations, and saturation of a challenging carbon-carbon double bond through a hydroboration/oxidation/xanthate formation/Barton-McCombie deoxygenation sequence as key transformations.

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Year:  2008        PMID: 18393518     DOI: 10.1021/ol800579j

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  STUDIES DIRECTED TOWARD THE SYNTHESIS OF NAKADOMARIN A.

Authors:  Thomas Haimowitz; Mark E Fitzgerald; Jeffrey D Winkler
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

2.  Total synthesis of (-)-nakadomarin A.

Authors:  Mark G Nilson; Raymond L Funk
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

3.  Enantioselective cyclization of enamide-ynes and application to the synthesis of the kopsifoline core.

Authors:  Britton K Corkey; Stephen T Heller; Yi-Ming Wang; F Dean Toste
Journal:  Tetrahedron       Date:  2013-07-08       Impact factor: 2.457

  3 in total

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