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Enantioselective Total Synthesis of 3β‐Hydroxy‐7β‐kemp‐8(9)‐en‐6‐one, a Diterpene Isolated from Higher Termites
Author(s) -
Wang Yuzhou,
Jäger Anne,
Gruner Margit,
Lübken Tilo,
Metz Peter
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.201708561
Subject(s) - diterpene , domino , enantioselective synthesis , total synthesis , ketone , moiety , stereochemistry , metathesis , chemistry , organic chemistry , catalysis , polymer , polymerization
The first total synthesis of the title diterpene was accomplished starting from the Wieland–Miescher ketone. A diastereoselective sulfa‐Michael addition enabled the generation of the delicate β,γ‐unsaturated ketone moiety, while the tetracyclic kempane skeleton was readily constructed through domino metathesis.