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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201704929
Subject(s) - annulation , total synthesis , cyclopropanation , chemistry , terpenoid , epoxide , aldehyde , substrate (aquarium) , euphorbia , organic chemistry , combinatorial chemistry , stereochemistry , catalysis , botany , biology , 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.