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Total Synthesis of Leucosceptroids A and B
Author(s) -
Guo Sheng,
Liu Jie,
Ma Dawei
Publication year - 2015
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.201410134
Subject(s) - total synthesis , ketyl , aldehyde , aldol reaction , chemistry , intramolecular force , olefin fiber , stereochemistry , citronellal , antifungal , radical cyclization , organic chemistry , radical , catalysis , biology , microbiology and biotechnology
Leucosceptroids A and B are sesterterpenoids with potent antifeedant and antifungal activities. A more efficient gram‐scale total synthesis of leucosceptroid B and the first total synthesis of leucosceptroid A are presented. The key transformations include an aldol reaction between a substituted dihydrofuranone and an ( S )‐citronellal‐derived aldehyde, a SmI 2 ‐mediated intramolecular ketyl–olefin radical cyclization, and final‐stage alcohol oxidation.