An expedient synthesis of 3-acyltetramic acids of the melophlin family from alpha-aminoesters and immobilized Ph3PCCO

The naturally occurring 3-acyltetramic acids (3-acylpyrrolidine-2,4-diones) melophlin A, B, C and G were prepared in few steps from alpha-aminoesters or their hydrochlorides by cyclization with Ph3PCCO under mild conditions. The employment of immobilized, polystyrene-bound ylide greatly simplifies t...

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Bibliographic Details
Published inTetrahedron Vol. 61; no. 9; pp. 2301 - 2307
Main Authors Schobert, R, Jagusch, C
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 28.02.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
phosphorus ylides
immobilized reagents
MIT ENAMINEN
DOMINO SYNTHESES
melophlins
tetramic acids
ENANTIOSELECTIVE TOTAL-SYNTHESIS
microwave
solid phase organic synthesis
MARINE SPONGE
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Summary:The naturally occurring 3-acyltetramic acids (3-acylpyrrolidine-2,4-diones) melophlin A, B, C and G were prepared in few steps from alpha-aminoesters or their hydrochlorides by cyclization with Ph3PCCO under mild conditions. The employment of immobilized, polystyrene-bound ylide greatly simplifies the removal of by-product Ph3PO and of other impurities. Various 3-acylation methods were assessed. (C) 2005 Elsevier Ltd. All rights reserved.
ISSN:0040-4020
DOI:10.1016/j.tet.2005.01.036