Asymmetric Total Syntheses of 8,9-Seco-ent-kaurane Diterpenoids Enabled by an Electrochemical ODI-[5+2] Cascade
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION(2021)
Abstract
An electrochemical ODI-[5+2] cascade reaction was developed which enables the rapid assembly of diversely functionalized bicyclo[3.2.1]octadienones from sensitive ethynylphenols. By combining a directed retro-aldol/aldol process, a [2,3]-sigmatropic rearrangement, and an Al(O-iPr)(3)-promoted reductive 1,3-transposition, the asymmetric total syntheses of five 8,9-seco-ent-kauranoids-(-)-shikoccin, (-)-O-methylshikoccin, (-)-epoxyshikoccin, (+)-O-methylepoxyshikoccin, and (+)-rabdo-hakusin-have been achieved in a concise and efficient manner.
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Key words
cascade reactions,electrochemistry,sigmatropic rearrangement,terpenoids,total synthesis
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