SYNTHESIS OF 10-CYANOVERTICILLENE AND ITS REACTIONS DIRECTED TOWARD THE VERTICILLOL SYNTHESIS

Directed toward the synthesis of verticillols, 10-cyanoverticillene 8 was settled as a key intermediate. Bond formation of cyano chloride 7 possessing secoverticillane skeleton to the key intermediate 8 with Li N(TMS)(2) at 60 degrees C proceeded smoothly with moderate yield. The tetrasubstituted double bond of 8 was selectively oxidized, providing the epoxyverticillene derivatives 15 and 16. Hydride reduction of the epoxides were attempted, giving unexpected results. Synthesis of dl-ve rticillene 13 was also presented.