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Stereocontrolled Total Syntheses of (−)‐Rotenone and (−)‐Dalpanol by 1,2‐Rearrangement and S N Ar Oxycyclizations
Author(s) -
Nakamura Kayo,
Ohmori Ken,
Suzuki Keisuke
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201609253
Subject(s) - rotenone , stereospecificity , chemistry , stereochemistry , alcohol , total synthesis , organic chemistry , catalysis , biochemistry , mitochondrion
The total syntheses of (−)‐rotenone and (−)‐dalpanol have been achieved by a group‐selective, stereospecific 1,2‐shift of an epoxy alcohol and S N Ar cyclizations. Three oxacycles are constructed, thus illustrating a versatile synthetic route to various rotenoids.