6 EudesmanolideからEremophilanolideへの変換

概要

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As a continuation of our study on the biogenetic-type transformation leading to the natural terpenoids, the conversion of the eudesmane-type sesquiterpenoids aiming at the eremophilane-type sesquiterpenoids has been undertaken and the object has been accomplished. After several attempts, treatment of 5α,6α-epoxy-dihydroalan-tolactone(7), an eudesmanolide epoxide, with HCOOH-acetone at reflux has been found to afford six products: product A(10%), B(34%), C(2.2%), D(2.0%), E(0.5%), and F(3.4%). Among them, two major products(A and B) have been elucidated to be the desired eremophilanolides(10 and 11) on the basis of physico-chemical evidences, while product C has been assigned 13. The structures of other minor products D, E, and F have been also suggested to be 16, 17, and 18, respectively. In order to correlate product B(11) to the known natural eremophilane-type derivatives, some chemical conversions have been attempted.
天然有機化合物討論会の論文
1973-10-01