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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.