Literature DB >> 15856117

Total synthesis of viridiofungin A.

Kenji Morokuma1, Keisuke Takahashi, Jun Ishihara, Susumi Hatakeyama.   

Abstract

Viridiofungin A, a member of amino alkyl citrate antibiotics from Trichoderma viride, was enantioselectively synthesized in naturally occurring form for the first time, employing regio- and stereoselective opening of the chiral glycidate with vinylmagnesium bromide and alkene cross metathesis of the citric acid core and hexadec-15-en-8-one as key steps.

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Year:  2005        PMID: 15856117     DOI: 10.1039/b500660k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  3 in total

Review 1.  Synthetic studies of viridiofungins, broad-spectrum antifungal agents and serine palmitoyl transferase inhibitors.

Authors:  Naoya Kumagai; Masakatsu Shibasaki
Journal:  J Antibiot (Tokyo)       Date:  2017-09-27       Impact factor: 2.649

2.  A stereoselective synthesis of (-)-viridiofungin A utilizing a TiCl(4)-promoted asymmetric multicomponent reaction.

Authors:  Arun K Ghosh; Jorden Kass
Journal:  Org Lett       Date:  2011-12-23       Impact factor: 6.005

3.  A unified synthetic strategy to the Cryptocarya family of natural products exploiting Anion Relay Chemistry (ARC).

Authors:  Bruno Melillo; Amos B Smith
Journal:  Org Lett       Date:  2013-04-24       Impact factor: 6.005

  3 in total

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