Printed in Great Britain. Pergamon Press Ltd. ©198 ITJPAC SESQUITERPENES- BIOSYNTHETIC STUDIES WITH 13C AND 2H MAGNETIC RESONANCE-

Abstract- Studies of the sesquiterpenes isolated from species of the Solanaceae under the stress of fungal infection are reviewed with emphasis on the biosynthetic pathways leading to their formation. These pathways have been examined primarily through incorporation experiments using doubly-labelled sodium acetate-'3C2 with '3Cmr characterization of the stress metabolites. Complementary evidence obtained from mevalonolactone-4,4-ci2 incorporation and 2Hmr is also described. The use of 2Hmr to monitor deuterium exchange in a variety of bicyclic ketones under homoenolization conditions is discussed. Certain of these homoenolization experiments lead to the development of a new synthesis for hirsutene and congeners which is outlined