40 ハイビスカスからのシクロプロペノイドとその誘導体の単離と構造(口頭発表の部)

概要

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In early studies on the seed germination inhibitors from a Hibiscus, we have isolated some new fatty acid methyl esters. In continuation of our studies, we isolated three cyclopropene compounds, methyl sterculate (1), malvalate (2) and 2-hydroxysterculate (7), as the active constituents along with two new compounds, 5 and 6. As malvalate (2) may be derived from sterculate (1) by a biological α-oxidation mechanism, 2-hydroxysterculate (7) would be an intermediate. The absolute configulation of the asymmetric carbon atom (C-2) of the compound 7 was determined as R by using a dibenzoate chilarity methode on the 1,2-diol derivative. We also found out a new ring opening oxidation of these cyclopropenoids by air to give a pair of conjugated enones, 3-A and 3-B, 4-A and 4-B, and 8-A and 8-B. From this air oxidation reaction and ozonolysis of the cyclopropenoids, we proposed a biogenetic pathway on the compounds isolated from Hibiscus rosa-sinensis.
天然有機化合物討論会の論文
1990-09-25