Reactions of cyclohexadienes. Part VIII. Stereoselective and nonstereoselective syntheses of (±)-juvabione

Abstract

Diels–Alder adducts from readily available dihydroanisoles and several αβ-unsaturated ketones have previously been shown to undergo acid-catalysed ring-opening to yield 4-substituted cyclohexenones. As the first example of the utility of this general process in natural product synthesis, a simple and efficient synthesis of (±)-juvabione diastereoisomers has been carried out. The synthesis was extended to yield (±)-juvabione in a stereoselective manner and confirms the recently revised stereochemistry of (±)-juvabione.