A Simple, Short, and Flexible Synthesis of Viridiofungin Derivatives

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 geo...

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Veröffentlicht in:	Journal of organic chemistry 2006-08, Vol.71 (16), p.6185-6191
Hauptverfasser:	Goldup, Stephen M, Pilkington, Christopher J, White, Andrew J. P, Burton, Andrew, Barrett, Anthony G. M
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkylation Amino Acids - chemistry Catalysis Chemistry Citrates - chemical synthesis Citrates - chemistry Esters - chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Malates - chemistry Molecular Structure Organic chemistry Preparations and properties
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Beschreibung
Zusammenfassung:	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.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo060931e