Synthesis of a Germination Self-inhibitor, (—)-gloeosporone, and Related Compounds and Evaluation of their Activities

Abstract

Synthesis of (—)-gloeosporone (la), isolated from spores of Colletotrichum gloeosporioides as a self-inhibitor for germination, and its three diastereomers was accomplished starting from (S)- and (R)-1-tridecen-8-ol obtained from their (S)-naphthyl ethylcarbamates (8a and 8b), both of which were isolated from the mixture of diastereoisomers derived from racemic 1-tridecen-8-ol (7) and the Pirkle reagent. Biological testing of the compounds showed weak self-inhibitor activity toward germination of the spores. © 1992, The Pharmaceutical Society of Japan. All rights reserved.