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Diastereoselective Total Synthesis of the Euphorbia Diterpenoid Pepluanol A: A Reductive Annulation Approach
Author(s) -
Xuan Jun,
Liu Zhaobo,
Zhu An,
Rao Peirong,
Yu Lei,
Ding Hanfeng
Publication year - 2017
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.201704929
Subject(s) - annulation , total synthesis , cyclopropanation , euphorbia , terpenoid , epoxide , chemistry , aldehyde , substrate (aquarium) , organic chemistry , stereochemistry , combinatorial chemistry , catalysis , biology , botany , ecology
A new titanium(III)‐catalyzed reductive annulation constructed a series of diversely functionalized 1,5‐diols in good to excellent yields with respect to a wide scope of vinyl epoxide‐aldehyde substrates. Taken together with a Diels–Alder reaction and a substrate‐controlled diastereoselective cyclopropanation as additional key steps, the synthetic utility of this novel method has been preliminarily explored by the first and concise total synthesis of the Euphorbia diterpenoid (±)‐pepluanol A.