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

Synthesis of benzofuranoid systems. IV. Total synthesis of cyperaquinone and conicaquinone

JK Macleod, BR Worth and RJ Wells

Australian Journal of Chemistry 31(7) 1533 - 1544
Published: 1978

Abstract

The total synthesis of the novel naturally occurring benzodifuroquinones, cyperaquinone (1) and conicaquinone (2), starting from phloroglucinol is described. A comparison of synthetic and natural compounds confirmed the original structural assignments. The key intermediate in the synthesis was the 3-methylbenzofuran (21) which was prepared in high yield by an internal site-specific base-catalysed Ar1-5 cyclization of the acetonyloxy derivative (19). The method has also been applied to the syntheses of linear furocoumarins and dibenzofurans.

https://doi.org/10.1071/CH9781533

© CSIRO 1978

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