A SIMPLE AND EFFICIENT ROUTE TOWARDS USEFULLY FUNCTIONALISED SIX AND SEVEN-MEMBERED RING SYSTEMS VIA α-HYDROXYCYCLOBUTANE REARRANGEMENT FOLLOWED BY RETROALDOL CLEAVAGE

Article abstract of DOI:10.1016/S0040-4020(01)80137-X

Acid-catalysed rearrangement of α-hydroxycyclobutane derivative 10 followed by retroaldol cleavage and oxidation in an one-pot operation furnishes 1β-methyl-1α,4α-cycloheptane dicarboxylic acid 12 in excellent yield.With proper selection of starting α-hydroxycyclobutane derivative this methodology leads to highly functionalised <5-7> and <5-6> fused ring systems 17 and 20 respectively.