Asymmetric Total Synthesis of (+)-Neooxazolomycin Using a Chirality-Transfer Strategy

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초록

The total synthesis of (+)-neooxazolomycin was achieved from the amino-acid d-serine. The efficiency of this approach is derived from the use of principles of memory of chirality and dynamic kinetic resolution in the intramolecular aldol reaction of a serine derivative to build the densely functionalized lactam framework and to install three contiguous stereocenters. The key intermediate was readily elaborated to the target natural product.

키워드

alkaloids; asymmetric synthesis; diastereoselectivity; natural products; total synthesis; STEREOSPECIFIC SYNTHESIS; NATURAL-PRODUCT; OXAZOLOMYCIN; BETA; ALPHA; 16-METHYLOXAZOLOMYCIN; DERIVATIVES; REAGENTS; MEMORY; CORE
제목
Asymmetric Total Synthesis of (+)-Neooxazolomycin Using a Chirality-Transfer Strategy
저자
Kim, Jae Hyun; Kim, Illan; Song, Yeonghun; Kim, Min Jung; Kim, Sanghee
DOI
10.1002/anie.201906158
발행일
2019-08
유형
Article
저널명
Angewandte Chemie International Edition
권
58
호
32
페이지
11018 ~ 11022