Literature DB >> 29712249

Stereocontrolled Total Synthesis of (+)-Altohyrtin A/Spongistatin 1.

Ian Paterson1, David Y-K Chen1, Mark J Coster1, Jose L Aceña1, Jordi Bach1, Karl R Gibson1, Linda E Keown1, Renata M Oballa1, Thomas Trieselmann1, Debra J Wallace1, Andrew P Hodgson1, Roger D Norcross1.   

Abstract

As an exceptionally potent antimitotic macrolide, altohyrtin A/spongistatin 1 shows great promise in cancer chemotherapy but its extreme scarcity in the natural sponges has halted its further preclinical development. A highly stereocontrolled total synthesis, which exploits boron-mediated aldol bond constructions, has been realized to provide, for the first time, a useful amount of synthetic material.
© 2001 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Entities:  

Keywords:  aldol reactions ; macrolides ; natural products ; total synthesis

Year:  2001        PMID： 29712249     DOI： 10.1002/1521-3773(20011105)40:21<4055::AID-ANIE4055>3.0.CO;2-H

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  6 in total

1.  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 2.  Natural Products in the "Marketplace": Interfacing Synthesis and Biology.

Authors:  Benjamin J Huffman; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2019-02-13       Impact factor: 15.419

Review 3.  Evolution of Anion Relay Chemistry: Construction of Architecturally Complex Natural Products.

Authors:  Yifan Deng; Amos B Smith
Journal:  Acc Chem Res       Date:  2020-04-09       Impact factor: 22.384

4.  Gold (III) Chloride-Catalyzed 6-endo-trig Oxa-Michael Addition Reactions for Diastereoselective Synthesis of Fused Tetrahydropyranones.

Authors:  Jennifer Ciesielski; David Lebœuf; Harry A Stern; Alison J Frontier
Journal:  Adv Synth Catal       Date:  2013-07-08       Impact factor: 5.837

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.  Catalytic asymmetric synthesis of geminal-dicarboxylates.

Authors:  Nisha Mistry; Stephen P Fletcher
Journal:  Chem Sci       Date:  2018-06-28       Impact factor: 9.825
  6 in total

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