The first asymmetric synthesis of (+)-methyl cembra-1,3,7,11-tetraene-16-carboxynate, a naturally occurring cembrane-type macrocyclic diterpene isolated from Sinularia mayi, was achieved via general approach by employing an intramolecular McMurry coupling and Sharpless asymmetric epoxidation as the key steps from readily available starting materials. The synthesis presented here verifies that the absolute configuration of compound 1 was assumed as 15R.
E,E) 3,7 Dimethyl 2,6 decadiene 1,10 diol(3), a terpenoid diol component of pheromonal secretion of the male queen butterfly, was synthesized stereoselectively from geraniol in seven steps. The key steps were the iodization rearrangement of 2,3 epoxy alcohol 6 and Claisen rearrangement of allyl vinyl ether 8.
The structure of a new natural epoxycembrene\|C isolated from soft coral \%Sarcophyton molle\% in of china the south sea , was amended as(\%11S, 12S\%)\|epoxycembrene\|C\% via\% the first asymmetric synthesis of(-)\|7,8\|epoxycembrene\|C and(+)\|11,12\|epoxycembrene\|C.
