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Isoxazole‐Assisted Direct Substitution of the Hydroxy Group in α‐Ketols: Introduction of Angular Substituents in a Polycyclic System
Author(s) -
Takikawa Hiroshi,
Hikita Katsuyoshi,
Suzuki Keisuke
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.200801577
Subject(s) - isoxazole , substituent , substitution (logic) , group (periodic table) , chemistry , ring (chemistry) , stereochemistry , unit (ring theory) , lewis acids and bases , medicinal chemistry , organic chemistry , computer science , mathematics , catalysis , programming language , mathematics education
The facile introduction of an angular substituent has become viable for the synthesis of natural products such as 2 . Ketol 1 serves to achieve this through the direct substitution of its hydroxy group by a Lewis acid (see scheme). The isoxazole unit facilitates the generation of a cation at the α‐position ( A ).