Literature DB >> 12605509

Total synthesis of (+)-spongistatin 1. An effective second-generation construction of an advanced EF Wittig salt, fragment union, and final elaboration.

Amos B Smith1, Wenyu Zhu, Shohei Shirakami, Chris Sfouggatakis, Victoria A Doughty, Clay S Bennett, Yasuharu Sakamoto.   

Abstract

A stereocontrolled, total synthesis of (+)-spongistatin 1 (1) has been achieved. Union of a second-generation EF Wittig salt (+)-3 with the advanced ABCD aldehyde (-)-4, followed by regioselective macrolactonization and global deprotection afforded (+)-spongistatin 1 (1). The longest linear sequence, 29 steps, proceeded in 0.5% overall yield.

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Year:  2003        PMID： 12605509     DOI： 10.1021/ol034037a

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


  12 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.  Design, synthesis, and biological evaluation of EF- and ABEF- analogues of (+)-spongistatin 1.

Authors:  Amos B Smith; Christina A Risatti; Onur Atasoylu; Clay S Bennett; Karen Tendyke; Qunli Xu
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

Review 3.  Advances in exploring the therapeutic potential of marine natural products.

Authors:  Xiao Liang; Danmeng Luo; Hendrik Luesch
Journal:  Pharmacol Res       Date:  2019-07-25       Impact factor: 7.658

Review 4.  Conformation-activity relationships of polyketide natural products.

Authors:  Erik M Larsen; Matthew R Wilson; Richard E Taylor
Journal:  Nat Prod Rep       Date:  2015-08       Impact factor: 13.423

5.  Achmatowicz Reaction and its Application in the Syntheses of Bioactive Molecules.

Authors:  Arun K Ghosh; Margherita Brindisi
Journal:  RSC Adv       Date:  2016-11-24       Impact factor: 3.361

6.  Design, synthesis, and biological evaluation of diminutive forms of (+)-spongistatin 1: lessons learned.

Authors:  Amos B Smith; Christina A Risatti; Onur Atasoylu; Clay S Bennett; Junke Liu; Hongsheng Cheng; Karen TenDyke; Qunli Xu
Journal:  J Am Chem Soc       Date:  2011-08-12       Impact factor: 15.419

7.  Intermolecular Cross-Acyloin Reactions by Fluoride-Promoted Additions of O-Silyl Thiazolium Carbinols.

Authors:  Alex K Mathies; Anita E Mattson; Karl A Scheidt
Journal:  Synlett       Date:  2009-01-01       Impact factor: 2.454

8.  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

9.  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

Review 10.  Recently confirmed apoptosis-inducing lead compounds isolated from marine sponge of potential relevance in cancer treatment.

Authors:  Magbubah Essack; Vladimir B Bajic; John A C Archer
Journal:  Mar Drugs       Date:  2011-09-20       Impact factor: 6.085
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