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

Intramolecular Diels-Alder Additions of Benzynes to Furans. Application to the Total Synthesis of Biflorin, and the Mansonone-E, I and F

WM Best and D Wege

Australian Journal of Chemistry 39(4) 647 - 666
Published: 1986

Abstract

Benzynes, generated either by the debromination of an appropriately substituted (o-dibromobenzene, or by the thermolysis of a substituted diazotized anthranilic acid, have been trapped intramolecularly by an attached furan moiety. One such adduct (41) has been transformed into 6,9-dimethylnaphtho[1,8-bc]pyran-3(2H)-one (43), which served as the key intermediate for the total synthesis of the title compounds, all of which are derivatives of 6,9-dimethylnaphtho[1,8-bc]pyran-7,8-quinone.

https://doi.org/10.1071/CH9860647

© CSIRO 1986

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