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Formation of α‐Hydroxy‐β‐diketones through Hydroxylation of Isoxazolium Salts: Stereoselective Approach to Angular cis‐ Diols in Polycyclic Systems
Author(s) -
Takikawa Hiroshi,
Takada Akiomi,
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.200801586
Subject(s) - stereoselectivity , hydroxylation , chemistry , diol , polyketide , hydrolysis , sodium salt , sodium hypochlorite , stereochemistry , organic chemistry , catalysis , enzyme , biosynthesis , inorganic chemistry
Only two steps were needed for the unprecedented oxidation of isoxazoles, which is exploited in the stereocontrolled introduction of an “angular cis ‐diol” characteristic of polyketide‐derived polycyclic natural products, such as 3 . In this two‐step process, 1) N‐methylation of isoxazole 1 and 2) stereoselective epoxidation of isoxazolium salt 2 with sodium hypochlorite followed by hydrolysis are carried out (Bn: benzyl).