Literature DB >> 11856018

Asymmetric total synthesis of (+)-brefeldin A from (S)-lactate by triple chirality transfer process and nitrile oxide cycloaddition.

Deukjoon Kim1, Jongkook Lee, Phil Jong Shim, Joong Inn Lim, Hyunil Jo, Sanghee Kim.   

Abstract

A novel synthesis of (+)-brefeldin A (1) has been accomplished on the basis of triple chirality transfer methodology, intramolecular ester enolate alkylation, and both intra- and intermolecular nitrile oxide cycloaddition strategies.

Entities:  

Year:  2002        PMID: 11856018     DOI: 10.1021/jo010743i

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  4 in total

1.  Transition structures of diastereoselective 1,3-dipolar cycloadditions of nitrile oxides to chiral homoallylic alcohols.

Authors:  Jennifer A R Luft; Kieche Meleson; K N Houk
Journal:  Org Lett       Date:  2007-01-25       Impact factor: 6.005

2.  Formal synthesis of (+)-brefeldin A: application of a zinc-mediated ring expansion reaction.

Authors:  Weimin Lin; Charles K Zercher
Journal:  J Org Chem       Date:  2007-05-12       Impact factor: 4.354

3.  trans-Hydrogenation: Application to a Concise and Scalable Synthesis of Brefeldin A.

Authors:  Michael Fuchs; Alois Fürstner
Journal:  Angew Chem Weinheim Bergstr Ger       Date:  2015-02-04

4.  Easy and direct conversion of tosylates and mesylates into nitroalkanes.

Authors:  Alessandro Palmieri; Serena Gabrielli; Roberto Ballini
Journal:  Beilstein J Org Chem       Date:  2013-03-14       Impact factor: 2.883

  4 in total

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