Literature DB >> 17286379

A modular approach to marine macrolide construction. 4. Assembly of C36-C51 and C29-C44 building blocks and evaluation of key coupling reactions targeting spongistatin 1 (altohyrtin A).

Stephane Ciblat1, Jungchul Kim, Catherine A Stewart, Jizhou Wang, Pat Forgione, Dean Clyne, Leo A Paquette.   

Abstract

Routes have been developed for the stereocontrolled elaboration of two highly functionalized sectors of spongistatin 1. The approach to ring F takes advantage of B-alkyl Suzuki-Miyaura coupling to install the C44-C45 bond. The E-ring pyran moiety was generated by acylation of an alpha-sulfonyl carbanion, the stereogenic centers of which were incorporated by sequential asymmetric aldol reactions. [structure: see text].

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Year:  2007        PMID： 17286379     DOI： 10.1021/ol063083i

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


  3 in total

1.  Exploiting pseudo C2-symmetry for an efficient synthesis of the F-ring of the spongistatins.

Authors:  Paul S Tanis; Joshua R Infantine; James L Leighton
Journal:  Org Lett       Date:  2013-10-10       Impact factor: 6.005

2.  2-Methylenetetrahydropyrans: efficient partners in the carbonyl ene reaction.

Authors:  Guohua Liang; Dakin T Sharum; Troy Lam; Nancy I Totah
Journal:  Org Lett       Date:  2013-11-11       Impact factor: 6.005

3.  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
  3 in total

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