Studies on the Synthesis of Eremophilane Sesquiterpenes. A Novel Entry into the Aristolane Ring System

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• The potassium salt of epimerically pure allylic alcohol 4a gave a 58% yield of a mixture consisting of 87% of compound 5 and 13% of product 6 when exposed to 18-crown-6 under normal rearrangement conditions (15 min, RT). Epimerically pure allylic alcohol 4b was not isolated in sufficient quantities for detailed examination. However, rearrangement of material enriched in 4b resulted in a 36% yield of a mixture of 5 and 6 in a ratio of 3.3:1, respectively
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