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

Synthesis of Aromatic Spiroacetals

MA Brimble, GM Horner and RJ Stevenson

Australian Journal of Chemistry 49(2) 189 - 196
Published: 1996

Abstract

The synthesis of aromatic spiroacetal ring systems related to the papulacandins is reported. ortho-Metalation of diisopropylbenzamide, followed by reaction with the electrophiles δ- valerolactone, γ- butyrolactone and γ-valerolactone, provided the keto alcohol adducts (10),(16) and (21) respectively. Reduction of the ketone followed by treatment with acid afforded phthalides (12),(18) and (23). Finally oxidative cyclization with iodobenzene diacetate provided the spiroacetals (7),(14) and (19).

https://doi.org/10.1071/CH9960189

© CSIRO 1996

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