The Journal of Organic Chemistry

Quassinoid synthesis via o-quinone Diels-Alder reactions

DD Weller, EP Stirchak

Index: Weller, Dwight D.; Stirchak, Eugene P. Journal of Organic Chemistry, 1983 , vol. 48, # 25 p. 4873 - 4879

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Citation Number: 39

Abstract

The reaction of 3, 5-disubstituted o-quinones (2a, 2c) and 4-chloro-3, 5-disubstituted o- quinones (2b, 2d) with simple dienes was investigated as a potential route to the quassinoid skeleton. Quinones 2a and 2c reacted in high yield at the 3, 4pcmition with only a small excess of diene. Attempted equilibration of the cis-fused cycloadducta to the trans-fused system failed due to the intervention of a stable enol form, as in 20. Compound 2c with ...