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. 2021 Jun 25;60(27):14892-14896.
doi: 10.1002/anie.202104410. Epub 2021 Jun 4.

Asymmetric Total Syntheses of 8,9-Seco-ent-kaurane Diterpenoids Enabled by an Electrochemical ODI-[5+2] Cascade

Bingnan Wang  1 , Zhaobo Liu  1 , Zhenzhong Tong  1 , Beiling Gao  1 , Hanfeng Ding  1   2
Affiliations

Asymmetric Total Syntheses of 8,9-Seco-ent-kaurane Diterpenoids Enabled by an Electrochemical ODI-[5+2] Cascade

Bingnan Wang et al. Angew Chem Int Ed Engl. .

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.

Keywords: cascade reactions; electrochemistry; sigmatropic rearrangement; terpenoids; total synthesis.

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References

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