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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Pigments of Fungi. XV. An Efficient, Unambiguous Route to Unsymmetrically Substituted Dibenzyl Acyloins and Their Use in the Synthesis of Fungus Pigments of the Pulvinone and Grevillin Types

M Gill, MJ Kiefel, DA Lally and A Ten

Australian Journal of Chemistry 43(9) 1497 - 1518
Published: 1990

Abstract

Dibenzyl acyloins including those bearing unsymmetrically disposed aryl residues are assembled in high yield by reaction between the O-trimethylsilyl ethers of arylacetaldehyde cyanohydrins and benzyl Grignard reagents. These acyloins are deprotonated with lithium diisopropylamide to afford alcoholate-enolate dianions which can be made to react with carbonyldiimidazole and with oxalyldiimidazole, respectively, to ultimately afford fungus pigments of the pulvinone and grevillin types.

https://doi.org/10.1071/CH9901497

© CSIRO 1990

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