Synthesis of dl-12-epiverticillol

The first synthesis of 12-epiverticillol , a constituent of a moss, Jackiella javanica, was elaborated in a dl-form by setting up 10-cyanoverticillene as a key intermediate. The C1–C2 bond of the intermediate is forced to take axial orientation as in the case of the verticillol. 10-cyanoverticillene was converted to γ-lactone , the cyclohexane ring of which was disclosed to take a boat conformation. Decarbonylation was achieved by application of Wilkinsonʹs catalyst to formyl MOM ether derived from , and final deprotection furnished the objective .