40 カウレン型ジテルペノイドの化学的変換

概要

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The transformations of enmein into (-)-isokaurene, beyerane, diterpene alkaloids and gibbane derivatives have been attempted. The transformation started with compounds 3〜8 prepared by the acyloin condensation reaction of unsaturated lactone ester 2 which had been derived from enmein. Ketoaldehyde 36, an oxidation product of 4, on Wolff-Kishner reductions gave (-)-kaurane, (-)-isokaurene and (-)-kaurene. The ratio of the products was due to the reaction condition. The treatment of hemiketal 40 with zinc, acetic acid and hydrochloric acid resulted in the formation of beyerane derivatives 42 and 43. Upon the photosensitized oxidation of 40 an allyl alcohol 29 was yielded. Further conversion of 29 into triol 26 has been attemped. The benzylic acid rearrangement of 3 yielded compound 18, which was converted into 24 via four steps of reactions.
天然有機化合物討論会の論文
1968-09-20