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Total Synthesis of the Isodon Diterpene Sculponeatin N
Author(s) -
Moritz Benjamin J.,
Mack Daniel J.,
Tong Liuchuan,
Thomson Regan J.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201310060
Subject(s) - diterpene , total synthesis , octane , chemistry , radical cyclization , ring closing metathesis , bicyclic molecule , metathesis , stereochemistry , salt metathesis reaction , ring (chemistry) , organic chemistry , polymerization , polymer
The total synthesis of sculponeatin N, a bioactive polycyclic diterpene isolated from Isodon sculponeatus , is reported. Key features of the synthesis include diastereoselective Nazarov and ring‐closing metathesis reactions, and a highly efficient formation of the bicyclo[3.2.1]octane ring system by a reductive radical cyclization.