Total Synthesis of 10-Isocyano-4-cadinene and Determination of Its Absolute Configuration
- 4 February 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 12 (5) , 904-907
Abstract
The first enantioselective total synthesis of 10-isocyano-4-cadinene, a marine sesquiterpene isolated from nudibranchs of the family Phyllidiidae, was achieved. The cadinene is expected to be a novel nontoxic antifouling agent. In the synthesis, an intermolecular Diels−Alder reaction and a SmI2-induced Barbier-type reaction were employed as key steps. The absolute configuration of 10-isocyano-4-cadinene was determined to be (1S, 6S, 7R, 10S) on the basis of the total synthesis. Antifouling activities against Balanus amphitrite with both enantiomers of 10-isocyano-4-cadinene were also evaluated.Keywords
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