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A Formal Asymmetric Synthesis of (+)‐Anatoxin‐a Using an Enantioselective Deprotonation Strategy on an Eight‐Membered Ring
Author(s) -
Aggarwal Varinder K.,
Humphries Paul S.,
Fenwick Ashley
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(19990712)38:13/14<1985::aid-anie1985>3.0.co;2-7
Subject(s) - enantioselective synthesis , deprotonation , ring (chemistry) , stereochemistry , formal synthesis , chemistry , organic chemistry , catalysis , ion
In only seven steps a formal synthesis of enantiomerically enriched (+)‐anatoxin‐a has been achieved. This was accomplished by utilizing a highly enantioselective desymmetrization of the eight‐membered ring ketone 1 to form 2 , and a novel cascade reaction to construct the 9‐azabicyclo[4.2.1]nonane skeleton.