Fungal products. Part V. The absolute stereochemistry of colletodiol and the structures of related metabolites of Colletotrichum capsici

Abstract

Colletoketol (2), colletol (3), and colletallol (4), three new co-metabolites of colletodiol (1)(10,11-dihydroxy-2,8-dimethyl-1,7-dioxacyclotetradeca-4,12-diene-6,14-dione), have been isolated from culture filtrates of Colletotrichum capsici and shown to be the 11-oxo-analogues of colletodiol, 11-deoxycolletodiol, and 10-deoxy-colletodiol, respectively. The absolute stereochemistry for colletodiol [i.e.(2R,8R,10R,11S)] has been assigned from chemical and optical rotatory evidence, and that for colletoketol [i.e.(2R, 8R,10R)] has been established by chemical correlation with colletodiol.