Isoxazole‐Assisted Direct Substitution of the Hydroxy Group in α‐Ketols: Introduction of Angular Substituents in a Polycyclic System | Zendy

Takikawa Hiroshi | Zendy; Hikita Katsuyoshi | Zendy; Suzuki Keisuke | Zendy

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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 ).

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