A novel and efficient total synthesis of the racemic form of the sesquiterpene (−)-aristolone (1) is presented. The key step involves the cupric sulfate catalyzed intramolecular cyclization of the diazoketone 27, which produces a mixture of products, the major component of which is (±)-aristolone.
An efficient total synthesis of the racemic forms of the novel tricyclic sesquiterpenes a-cubebene (1) and 8-cubebene (2) is described. The key step of this synthesis involved the cupric sulfate catalyzed intramolecular cyclization of the olefinic diazoketone 3, which produced, in high yield, (+)-8-cubebene norketone (24) and (f )-l,6-epi-p-cubebene norketone (25), in a ratio of approximately 3:5, respectively.
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