Literature DB >> 16872204

A simple, short, and flexible synthesis of viridiofungin derivatives.

Stephen M Goldup1, Christopher J Pilkington, Andrew J P White, Andrew Burton, Anthony G M Barrett.   

Abstract

Described herein is a simple, flexible, and efficient synthesis of the skeleton of the viridiofungins, a family of microbial secondary metabolites. The synthesis utilizes an asymmetric aldol reaction of a chiral oxazolidinone, a diastereoselective alkylation of a chiral 1,3-dioxolan-2-one, and a geometrically selective alkene cross-metathesis reaction as the key C-C bond-forming steps.

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Year:  2006        PMID: 16872204     DOI: 10.1021/jo060931e

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


  5 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.  Silylene transfer to alpha-keto esters and application to the synthesis of gamma-lactones.

Authors:  Brett E Howard; K A Woerpel
Journal:  Tetrahedron       Date:  2009-09-01       Impact factor: 2.457

3.  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

4.  Effective immobilisation of a metathesis catalyst bearing an ammonium-tagged NHC ligand on various solid supports.

Authors:  Krzysztof Skowerski; Jacek Białecki; Stefan J Czarnocki; Karolina Żukowska; Karol Grela
Journal:  Beilstein J Org Chem       Date:  2016-01-05       Impact factor: 2.883

5.  In vitro studies of maleidride-forming enzymes.

Authors:  Sen Yin; Steffen Friedrich; Vjaceslavs Hrupins; Russell J Cox
Journal:  RSC Adv       Date:  2021-04-21       Impact factor: 3.361

  5 in total

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