Natural acetylenes. Part XXXIII. The biogenesis of the C9 diacetylenic triol from the fungus Clitocybe rhizophora velen

Labelled diethyl malonate, methyl oleate, methyl linoleate, and methyl crepenynate (CH3·[CH2]4·CC·CH2·CHCH·[CH2]7·CO2Me) were all incorporated into the triol CH3·CH2·CH(OH)·[CC]2·CH(OH)·CH2·OH by cultures of the fungus in the expected manner. Specifically labelled (14C and 3H) lachnophyllum ester (CH3·CH2·CH2·[CC]2·CHCH·CO2Me) has been synthesised and also shown to be a precursor of the triol.A new metabolite, CH3[graphic omitted]CH·[CC]2·CH2·CH2·OH, has been isolated.