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A furyl sesquiterpene pleraplysillin-1 (1), which possesses the ochtodane skeleton (2) in the molecule, was synthesized regio- and stereoselectively starting from the ochtodane type monoterpene (5). Two approaches were investigated: One is the route by way of the benzenesulfenyl chloride addition to a sesquiterpene (9) or (13) which involve the whole carbon framework of 1 and the exocyclic E- or Z-double bond, and the other involves the regioselective formation of the endocyclic double bond of the ochtodane synthon (15) utilizing the hydroxylassisted epoxide opening reaction followed by homologation with the 3-furylmethyl moiety. In both of the routes the geometry of the exocyclic double bond of the ochtodane synthon played an important role in the regioselective formation of the endocyclic double bond in 1.

5-Alkyl-6,8-dioxabicyclo[3.2.l]octanes with sulfur-containing substituents at the C(3)-position were found to undergo an unusual substitution reaction with mercaptans in the presence of the Lewis acids providing the corresponding 3-sulfenyl derivatives.

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