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Total Synthesis of the Diterpenoid (+)‐Harringtonolide
Author(s) -
Zhang HaiJun,
Hu Lin,
Ma Zhiqiang,
Li Ruining,
Zhang Zhen,
Tao Cheng,
Cheng Bin,
Li Yun,
Wang Huifei,
Zhai Hongbin
Publication year - 2016
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.201605879
Subject(s) - tropone , intramolecular force , cycloaddition , rhodium , terpenoid , total synthesis , chemistry , stereochemistry , catalysis , organic chemistry
Described herein is the first asymmetric total synthesis of (+)‐harringtonolide, a natural diterpenoid with an unusual tropone imbedded in a cagelike framework. The key transformations include an intramolecular Diels–Alder reaction and a rhodium‐complex‐catalyzed intramolecular [3+2] cycloaddition to install the tetracyclic core as well as a highly efficient tropone formation.