(+)-Ieodomycin B와 유도체의 광학이성질 선택적 합성: 합성과 생리활성 측정

Title
(+)-Ieodomycin B와 유도체의 광학이성질 선택적 합성: 합성과 생리활성 측정
Alternative Title
Enantioselective Total Synthesis of (+)-Ieodomycin B and its Optical Isomers: Synthesis and Biological Evaluation
Author(s)
최두봉; 이지훈; 이연주; 이희승; 이종석
KIOST Author(s)
Lee, Jihoon(이지훈)Lee, Yeon Ju(이연주)Lee, Hyi Seung(이희승)Lee, Jong Soo(이종수)
Publication Year
2019-08-28
Abstract
Ieodomycins comprise a family of fatty acids derived from a marine Bacillus sp.. In this presentation, an enantioselective total synthesis of (+)-ieodomycin B along with its three other optical isomers is described. The key steps of the synthesis employ Keck asymmetric allylation to provide an enantiopure homoallylic alcohol, Wipf’s modification of Negishi’s carboalumination reaction, Sharpless asymmetric dihydroxylation, and Pinner reaction. In the final step, Stille cross-coupling reaction was employed to install the terminal 1,3-diene moiety. The main advantage of the present synthesis is highlighted in the introduction of the terminal 1,3-diene at the very end of the synthesis, which enables chemical diversity by the late-stage modification of the corresponding lactone. Furthermore, the synthesized compounds were evaluated for their inhibitory activities against HMG(3-hydroxy-3-methylglutaryl)-CoA reductase. The results will be described and discussed further.
URI
https://sciwatch.kiost.ac.kr/handle/2020.kiost/22415
Bibliographic Citation
ACS National Meeting, San Diego, pp.1 - 2, 2019
Publisher
미국화학회
Type
Conference
Language
English
Publisher
미국화학회
Related Researcher
Research Interests

Marine Natural Products,Organic Chemistry,해양천연물,유기화학

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