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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201505251
Subject(s) - enantioselective synthesis , chemistry , total synthesis , stereoselectivity , octane , ring (chemistry) , phosphine , stereochemistry , radical cyclization , organic chemistry , catalysis
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.