Literature DB >> 10814408

A modular approach to marine macrolide construction. 3. Enantioselective synthesis of the C1-C28 sector of spongistatin 1 (altohyrtin A).

D Zuev1, L A Paquette.   

Abstract

[structure: see text] A completely stereocontrolled approach to assembly of the major C1-C28 subunit of spongistatin 1 (altohyrtin A) is described. Key steps included the control of two asymmetric aldols by means of Fujita-Nagao (chiral N-acyl-1,3-thiazolidine-2-thione auxiliary) and Mukaiyama (BF3 x OEt2-promoted enolsilane coupling) protocols in complex settings.

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Year:  2000        PMID： 10814408     DOI： 10.1021/ol0000049

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


  2 in total

1.  Spongipyran Synthetic Studies. Total Synthesis of (+)-Spongistatin 2.

Authors:  Amos B Smith; Qiyan Lin; Victoria A Doughty; Linghang Zhuang; Mark D McBriar; Jeffrey K Kerns; Armen M Boldi; Noriaki Murase; William H Moser; Christopher S Brook; Clay S Bennett; Kiyoshi Nakayama; Masao Sobukawa; Robert E Lee Trout
Journal:  Tetrahedron       Date:  2009-08-15       Impact factor: 2.457

2.  Gram-scale synthesis of (+)-spongistatin 1: development of an improved, scalable synthesis of the F-ring subunit, fragment union, and final elaboration.

Authors:  Amos B Smith; Takashi Tomioka; Christina A Risatti; Jeffrey B Sperry; Chris Sfouggatakis
Journal:  Org Lett       Date:  2008-08-28       Impact factor: 6.005
  2 in total

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