Reductive, radical-induced cyclization of 5-hexenals as a biomimetic model of the chemistry of secologanin formation

T Ikeda, S Yue, CR Hutchinson

文献索引：Ikeda, Takafumi; Yue, Stephen; Hutchinson, C. Richard Journal of Organic Chemistry, 1985 , vol. 50, # 25 p. 5193 - 5199

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被引用次数: 39

摘要

A model reaction for studying the mechanism of the biological conversion of the iridoid loganin (1) to the secoiridoid secologanin (2) is the reductive, radical-induced cyclization of secologanin tetraacetate (4) to loganin tetraacetate. Treatment of 4 with Mg and Me3SiCl in THF at room temperature gives a mixture of the four possible C-6 and C-7 epimers of loganin tetraacetate in which the natural stereochemistry predominates. This result ...