30 Spirovetivane類の合成

概要

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Considerable attention has been paid to the synthesis of natural spirovetivanes, which involve various sesquiterpenes with different stereochemistry; that is, β-vetivone (1), hinesol (2), agarospirol (3), solavetivone (4), oxylubimin (7), and others differ each other in stereochemistry at C-4, C-5, and C-7 of the spirovetivane skeleton. We describe herein a new and efficient process leading to the synthesis of most of the sesquiterpenes. The process is summarized in Scheme 1, which consists of two major steps; (i) the Diels-Alder reaction (Schemes 3 and 6) of substituted dihydroanisoles(Schemes 2 and 6) and methyl acrylate or its equivalents followed by transformation for the second key reaction, and (ii) acid cleavage of the resulting bicyclooctanes and subsequent π-cyclization, giving the spirovetivanes practically in a single step (Scheme 4). The relevant relative stereochemistry between C-4 and C-5 and between C-7 and C-5 could be controlled in the first and second steps, respectively. Examination of reagents and reaction conditions resulted in stereoselective and short-step syntheses of β-vetivone (1), hinesol (2), β-vetispirene, and solavetivone (4).
天然有機化合物討論会の論文
1979-09-20