Literature DB >> 19441795

Total synthesis of brevenal.

Hiroyoshi Takamura1, Shigetoshi Kikuchi, Yuichi Nakamura, Yuji Yamagami, Takayuki Kishi, Isao Kadota, Yoshinori Yamamoto.   

Abstract

A total synthesis of brevenal is described. The pentacyclic ether core was constructed by the intramolecular allylation of alpha-acetoxy ether and subsequent ring-closing metathesis. Both of the diene side chains were introduced by Wittig olefination and a Horner-Wadsworth-Emmons reaction, respectively, in a highly stereoselective manner.

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Year:  2009        PMID： 19441795     DOI： 10.1021/ol900769d

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


  5 in total

Review 1.  The development of endo-selective epoxide-opening cascades in water.

Authors:  Christopher J Morten; Jeffery A Byers; Aaron R Van Dyke; Ivan Vilotijevic; Timothy F Jamison
Journal:  Chem Soc Rev       Date:  2009-09-16       Impact factor: 54.564

2.  A highly convergent approach toward (-)-brevenal.

Authors:  Michael T Crimmins; Mariam Shamszad; Anita E Mattson
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

3.  Total synthesis of brevenal.

Authors:  Yuan Zhang; John Rohanna; Jie Zhou; Karthik Iyer; Jon D Rainier
Journal:  J Am Chem Soc       Date:  2011-02-15       Impact factor: 15.419

Review 4.  Recent progress in neuroactive marine natural products.

Authors:  Ryuichi Sakai; Geoffrey T Swanson
Journal:  Nat Prod Rep       Date:  2014-01-17       Impact factor: 13.423

5.  Total synthesis of brevisamide.

Authors:  Olugbeminiyi O Fadeyi; Craig W Lindsley
Journal:  Org Lett       Date:  2009-09-03       Impact factor: 6.005
  5 in total

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