An enantioselective synthesis of (+)-polyoxamic acid via phase-transfer catalytic conjugate addtion and asymmetric dihydroxylation

Title
An enantioselective synthesis of (+)-polyoxamic acid via phase-transfer catalytic conjugate addtion and asymmetric dihydroxylation
Author(s)
이연주; 주상섭; 박형근
KIOST Author(s)
Lee, Yeon Ju(이연주)
Alternative Author(s)
이연주
Publication Year
2012-06-26
Abstract
A new efficient stereoselective synthesis of (+)-polyoxamic acid, the major component of the polyoxin family of antifungal antibiotics, is reported. Starting from a commercially available glycine derived Schiff base, (+)-polyoxamic acid was obtained in 46% overall yield after 7 linear steps. Enantioselective phase-transfer catalytic Michael reaction (99% yield, 96% ee) and diastereoselctvie dihydroxylation (98% yield, 94% de) are very efficient key reactions. In both, cinchona derivatives were used as stereoselectivity control element, which make this synthesis more practical. was obtained in 46% overall yield after 7 linear steps. Enantioselective phase-transfer catalytic Michael reaction (99% yield, 96% ee) and diastereoselctvie dihydroxylation (98% yield, 94% de) are very efficient key reactions. In both, cinchona derivatives were used as stereoselectivity control element, which make this synthesis more practical.
URI
https://sciwatch.kiost.ac.kr/handle/2020.kiost/27625
Bibliographic Citation
13th tetrahedron symposium, pp.72, 2012
Publisher
elsevier
Type
Conference
Language
English
Publisher
elsevier
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