Literature DB >> 10891180

Synthesis of the alleged structure of sclerophytin A. The setting of two oxygen bridges within the fused cyclodecanol B ring is not Nature's Way.

L A Paquette1, O M Moradei, P Bernardelli, T Lange.   

Abstract

[reaction: see text] The structure attributed to sclerophytin A, a cytotoxic soft coral metabolite, was synthesized in an enantioselective manner from (5S)-5-(d-menthyloxy)-2(5H)-furanone. The spectral properties and polarity of the synthetic product require that the structural assignment to the natural material be revised.

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Year:  2000        PMID： 10891180     DOI： 10.1021/ol000083o

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


  6 in total

1.  A general route toward the synthesis of the cladiellin skeleton utilizing a SmI2-mediated cyclization.

Authors:  Gary A Molander; Barbara Czakó; David J St Jean
Journal:  J Org Chem       Date:  2006-02-03       Impact factor: 4.354

2.  Establishing the absolute configuration of the asbestinins: enantioselective total synthesis of 11-acetoxy-4-deoxyasbestinin D.

Authors:  Michael T Crimmins; J Michael Ellis
Journal:  J Am Chem Soc       Date:  2005-12-14       Impact factor: 15.419

3.  Total syntheses of (+)-vigulariol and (-)-sclerophytin A.

Authors:  Michael T Crimmins; Christina S Stauffer; Mark C Mans
Journal:  Org Lett       Date:  2011-08-19       Impact factor: 6.005

4.  A unified strategy for enantioselective total synthesis of cladiellin and briarellin diterpenes: total synthesis of briarellins E and F and the putative structure of alcyonin and revision of its structure assignment.

Authors:  Olivier Corminboeuf; Larry E Overman; Lewis D Pennington
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

5.  Enantioselective synthesis of (-)-sclerophytin A by a stereoconvergent epoxide hydrolysis.

Authors:  Bin Wang; Armando P Ramirez; Justin J Slade; James P Morken
Journal:  J Am Chem Soc       Date:  2010-10-28       Impact factor: 15.419

6.  Synthesis and Evaluation of a 2,11-Cembranoid-Inspired Library.

Authors:  Amanda J Welford; John J Caldwell; Manjuan Liu; Meirion Richards; Nathan Brown; Cara Lomas; Graham J Tizzard; Mateusz B Pitak; Simon J Coles; Suzanne A Eccles; Florence I Raynaud; Ian Collins
Journal:  Chemistry       Date:  2016-03-01       Impact factor: 5.236
  6 in total

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