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Total Synthesis of Cryptotrione
Author(s) -
Lyu MaoYun,
Zhong Zhuliang,
Lo Vanessa KarYan,
Wong Henry N. C.,
Peng XiaoShui
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202009255
Subject(s) - cycloisomerization , stereocenter , chemistry , abietane , polyene , diterpene , stereochemistry , enyne , total synthesis , lewis acids and bases , conjugate , enantioselective synthesis , catalysis , organic chemistry , mathematical analysis , mathematics
The total synthesis of cryptotrione ( 1 ) was enabled by substrate‐controlled diastereoselective construction of the bicyclo[3.1.0]hexene framework through platinum‐catalyzed enyne cycloisomerization and Lewis acid induced polyene cyclization to construct the abietane‐type tricyclic diterpene skeleton. The stereogenic tertiary carbon center in the side chain was installed in a diastereodivergent manner by conjugate addition reactions.