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Remote Stereoinductive Intramolecular Nitrile Oxide Cycloaddition: Asymmetric Total Synthesis and Structure Revision of (-)-11 beta-Hydroxycurvularin
Journal article   Peer reviewed

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

Hyeonjeong Choe, Thuy Trang Pham, Joo Yun Lee, Muhammad Latif, Haeil Park, Young Kee Kang and Jongkook Lee
Journal of organic chemistry, Vol.81(6), pp.2612-2617
18/03/2016
PMID: 26894643

Abstract

Chemistry Chemistry, Organic Physical Sciences Science & Technology
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.

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