The first synthesis of 12-epiverticillol 2, a constituent of a moss, Jackiella javanica, was elaborated in a dl-form by setting up 10-cyanoverticillene 3 as a key intermediate. The C1-C2 bond of the intermediate 3 is forced to take axial orientation as in the case of the verticillol. 10-cyanoverticillene 3 was converted to γ-lactone 11, the cyclohexane ring of which was disclosed to take a boat conformation. Decarbonylation was achieved by application of Wilkinson's catalyst to formyl MOM ether 25 derived from 11, and final deprotection furnished the objective 2.
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry