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Enantioselective Total Synthesis of the Nonisoprenoid Sesquiterpene (−)‐Kumausallene
Author(s) -
Evans P. Andrew,
Murthy V. Srinivasa,
Roseman Jamie D.,
Rheingold Arnold L.
Publication year - 1999
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/(sici)1521-3773(19991102)38:21<3175::aid-anie3175>3.0.co;2-m
Subject(s) - enantioselective synthesis , sesquiterpene , total synthesis , bicyclic molecule , core (optical fiber) , stereochemistry , unit (ring theory) , chemistry , computer science , mathematics , organic chemistry , catalysis , telecommunications , mathematics education
An acyl radical cyclization to form the bicyclic core of (−)‐kumausallene ( 1 ) was the key feature in the 14‐step, enantioselective synthesis. This work demonstrates that the bromoallene unit is robust enough to withstand multiple synthetic operations and provides the unambiguous assignment of the absolute configuration of the bromoallene.