44 トリキナン型テルペン類の合成研究

概要

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Synthetic effort toward two sesquiterpenes, silphinene (4) and senoxydene (5), and a diterpene, laurenene (6), is described. Since these compounds contain common structural feature, angular triquinane with very similar substitution pattern, we have formulated a synthetic strategy starting from the readily available dicyclopentadiene and branching off at certain points to culminate in the synthesis of all three, as is shown in Scheme I. Following reaction sequence shown in Scheme II and III, silphinene (4) was synthesized. Synthesis of senoxydene (5) branched off at synthetic intermediate 20 and, by the sequence shown in Scheme IV and V, a compound having the structure proposed by Bohlmann was achieved. However, PMR spectrum of the compound was not identical with the published data. There is a possibility that the natural product has a different structure. The synthesis of laurenene (6) was anticipated to be most difficult and therefore challenging, because of severe steric congestion. Although it has not yet been accomplished, the progress will be reported.
天然有機化合物討論会の論文
1983-09-15