Literature DB >> 11869127

Spongistatin synthetic studies. An efficient, second-generation construction of an advanced ABCD intermediate.

Amos B Smith1, Victoria A Doughty, Chris Sfouggatakis, Clay S Bennett, Jyunichi Koyanagi, Makoto Takeuchi.   

Abstract

[reaction: see text] A short, efficient, and stereocontrolled synthesis of (-)-4, an advanced ABCD subunit of the spongistatins, has been achieved. Central to the synthetic strategy is the multicomponent linchpin union of silyl dithianes with epoxides to access both the AB and CD fragments. Fragment coupling was then achieved via an efficient stereoselective aldol reaction. The linear sequence required 22 steps and proceeded in 4.0% overall yield.

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Year:  2002        PMID： 11869127     DOI： 10.1021/ol017273z

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


  6 in total

1.  Spongipyran Synthetic Studies. Evolution of a Scalable Total Synthesis of (+)-Spongistatin 1.

Authors:  Amos B Smith; Chris Sfouggatakis; Christina A Risatti; Jeffrey B Sperry; Wenyu Zhu; Victoria A Doughty; Takashi Tomioka; Dimitar B Gotchev; Clay S Bennett; Satoshi Sakamoto; Onur Atasoylu; Shohei Shirakami; David Bauer; Makoto Takeuchi; Jyunichi Koyanagi; Yasuharu Sakamoto
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

2.  Enantioselective synthesis and structure revision of solandelactone E.

Authors:  Jennifer E Davoren; Stephen F Martin
Journal:  J Am Chem Soc       Date:  2007-01-24       Impact factor: 15.419

3.  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

4.  Convergent Synthesis of the C1-C29 Framework of Amphidinolide F.

Authors:  Filippo Romiti; Ludovic Decultot; J Stephen Clark
Journal:  J Org Chem       Date:  2022-06-08       Impact factor: 4.198

5.  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

6.  Exploration of an epoxidation-ring-opening strategy for the synthesis of lyconadin A and discovery of an unexpected Payne rearrangement.

Authors:  Brad M Loertscher; Yu Zhang; Steven L Castle
Journal:  Beilstein J Org Chem       Date:  2013-06-18       Impact factor: 2.883
  6 in total

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