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

Wang Bingnan | Zendy; Liu Zhaobo | Zendy; Tong Zhenzhong | Zendy; Gao Beiling | Zendy; Ding Hanfeng | Zendy

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

Author(s) -

Wang Bingnan,

Liu Zhaobo,

Tong Zhenzhong,

Gao Beiling,

Ding Hanfeng

Publication year - 2021

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.202104410

Subject(s) - aldol reaction , cascade , chemistry , total synthesis , stereochemistry , sigmatropic reaction , electrochemistry , combinatorial chemistry , organic chemistry , catalysis , electrode , chromatography

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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