Development of efficient asymmetric synthetic method for marine natural products contained novel hexahydrocoumalin skeleton

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Synthetic study of marine diterpenoid, kitungolide B, contained novel hexahydrocoumalin skeleton was occurred. Reformatsky reaction with zinc, ethyl bromoacetate and aldehyde compound, whichobtained the 3-methyl-2-buten-1-ol via three steps, was carried out. As the results, the nucleophilic attack to the aldehyde moiety, cyclization and elimination reactions were proceeded simultaneously, the desired unsaturated lactone was obtained. The 1,4-addition to the unsaturated lactone followed by ring closing metathesis was provided trans-fused bicyclic lactone compound. Further study of the construction of hexahydrocoumalin skeleton is now on going.