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Dynamic Stereochemistry Transfer in a Transannular Aldol Reaction: Total Synthesis of Hypocrellin A
Author(s) -
O'Brien Erin M.,
Morgan Barbara J.,
Kozlowski Marisa C.
Publication year - 2008
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.200800734
Subject(s) - aldol reaction , stereocenter , intramolecular force , chemistry , ring (chemistry) , stereochemistry , aldol condensation , diketone , total synthesis , enantioselective synthesis , organic chemistry , catalysis
A dynamic approach : The key step in the total synthesis of hypocrellin A involves a potentially biomimetic 1,8‐diketone aldol reaction, which constructs the seven‐membered ring. The helical configuration is established first from an axially chiral biaryl unit and is then used in a dynamic stereochemical transfer process to form the remaining stereocenters in the intramolecular aldol reaction (see scheme).