Literature DB >> 19694486

An asymmetric total synthesis of brevisamide.

Arun K Ghosh1, Jianfeng Li.   

Abstract

An enantioselective synthesis of marine alkaloid brevisamide was accomplished in a convergent manner. The synthesis utilized an enantioselective hetero-Diels-Alder reaction which sets three chiral centers in compound 11. The synthesis also features a modified Wolff-Kishner reduction, Rubottom oxidation, and Suzuki-Miyaura coupling to furnish brevisamide.

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Year:  2009        PMID： 19694486      PMCID： PMC2812931          DOI： 10.1021/ol901691d

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


  12 in total

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Authors:  M S Lee; D J Repeta; K Nakanishi; M G Zagorski
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Authors:  Andrea J Bourdelais; Henry M Jacocks; Jeffrey L C Wright; Paul M Bigwarfe; Daniel G Baden
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4.  Highly Enantio- and Diastereoselective Hetero-Diels-Alder Reactions Catalyzed by New Chiral Tridentate Chromium(III) Catalysts.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-08       Impact factor: 15.336

5.  The B-Alkyl Suzuki-Miyaura Cross-Coupling Reaction: Development, Mechanistic Study, and Applications in Natural Product Synthesis A list of abbreviations can be found at the end of the article.

Authors:  Sherry R. Chemler; Dirk Trauner; Samuel J. Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2001-12-17       Impact factor: 15.336

6.  Diastereoselective zinco-cyclopropanation of chiral allylic alcohols with gem-dizinc carbenoids.

Authors:  Jean-François Fournier; Simon Mathieu; André B Charette
Journal:  J Am Chem Soc       Date:  2005-09-28       Impact factor: 15.419

7.  Three-component synthesis of alpha,beta-cyclopropyl-gamma-amino acids.

Authors:  Peter Wipf; Corey R J Stephenson
Journal:  Org Lett       Date:  2005-03-17       Impact factor: 6.005

8.  Total synthesis of the proposed structure of brevenal.

Authors:  Haruhiko Fuwa; Makoto Ebine; Makoto Sasaki
Journal:  J Am Chem Soc       Date:  2006-08-02       Impact factor: 15.419

9.  (9Z)- and (11Z)-8-methylretinals for artificial visual pigment studies: stereoselective synthesis, structure, and binding models.

Authors:  Rosana Alvarez; Marta Domínguez; Yolanda Pazos; Fredy Sussman; Angel R de Lera
Journal:  Chemistry       Date:  2003-12-05       Impact factor: 5.236

10.  Total synthesis and structural confirmation of brevisamide, a new marine cyclic ether alkaloid from the dinoflagellate Karenia brevis.

Authors:  Takefumi Kuranaga; Tomohiro Shirai; Daniel G Baden; Jeffrey L C Wright; Masayuki Satake; Kazuo Tachibana
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005
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  5 in total

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4.  Capturing the essence of organic synthesis: from bioactive natural products to designed molecules in today's medicine.

Authors:  Arun K Ghosh
Journal:  J Org Chem       Date:  2010-10-11       Impact factor: 4.354

5.  Atom-Economical Cross-Coupling of Internal and Terminal Alkynes to Access 1,3-Enynes.

Authors:  Mingyu Liu; Tianhua Tang; Omar Apolinar; Rei Matsuura; Carl A Busacca; Bo Qu; Daniel R Fandrick; Olga V Zatolochnaya; Chris H Senanayake; Jinhua J Song; Keary M Engle
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  5 in total

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