Remote Stereoinductive Intramolecular Nitrile Oxide Cycloaddition: Asymmetric Total Synthesis and Structure Revision of (-)-11β-Hydroxycurvularin

Choe, Hyeonjeong; Pham, Thuy Trang; Lee, Joo Yun; Latif, Muhammad; Park, Haeil; Kang, Young Kee; Lee, Jongkook

doi:10.1021/acs.joc.5b02760

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Remote Stereoinductive Intramolecular Nitrile Oxide Cycloaddition: Asymmetric Total Synthesis and Structure Revision of (-)-11β-Hydroxycurvularin

Choe, Hyeonjeong;
Pham, Thuy Trang;
Lee, Joo Yun;
Latif, Muhammad;
Park, Haeil;
... Lee, Jongkook;
외 1명

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24

초록

The first total synthesis and structure revision of (-)-11 beta-hydroxycurvularin (1b), a macrolide possessing a beta-hydroxyketone moiety, were accomplished. The beta-hydroxyketone moiety in this natural product was introduced by cleavage of the N-O bond in an isoxazoline ring that was formed diastereoselectively in a 1,5-remote stereocontrolled fashion by employing intramolecular nitrile oxide cycloaddition.

키워드

DIELS-ALDER REACTION; CURVULARIN-TYPE METABOLITES; FORMAL TOTAL-SYNTHESIS; CITREO-VIRIDE-B; EFFICIENT SYNTHESIS; SYNTHASE EXPRESSION; CONCISE SYNTHESES; MACROCYCLIZATION; (S)-CURVULARIN; RHIZOSPHERE

제목: Remote Stereoinductive Intramolecular Nitrile Oxide Cycloaddition: Asymmetric Total Synthesis and Structure Revision of (-)-11β-Hydroxycurvularin

저자: Choe, Hyeonjeong; Pham, Thuy Trang; Lee, Joo Yun; Latif, Muhammad; Park, Haeil; Kang, Young Kee; Lee, Jongkook

DOI: 10.1021/acs.joc.5b02760

발행일: 2016-03-18

유형: Article

저널명: The Journal of Organic Chemistry

권: 81

호: 6

페이지: 2612 ~ 2617