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Enantioselective Total Synthesis of (−)‐Hosieine A
Author(s) -
Ouyang Jie,
Yan Rui,
Mi Xianwei,
Hong Ran
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.201505251
Subject(s) - enantioselective synthesis , chemistry , radical cyclization , stereoselectivity , stereochemistry , total synthesis , octane , ring (chemistry) , ene reaction , markovnikov's rule , organic chemistry , catalysis , regioselectivity
The first total synthesis of (−)‐hosieine A was accomplished and features an unprecedented nitroso–ene cyclization to construct the 2‐azabicyclo[3.2.1]octane ring system. Phosphine‐enabled stereoselective bromohydrination provided interesting mechanistic insights into the anti‐Markovnikov process. Also noteworthy is the retention of stereochemistry at C9 in the facile radical debromination initiated by Et 3 B/air.