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

The Journal of Organic Chemistry
Hyeonjeong ChoeJongkook Lee

Abstract

The first total synthesis and structure revision of (-)-11β-hydroxycurvularin (1b), a macrolide possessing a β-hydroxyketone moiety, were accomplished. The β-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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Citations

Feb 14, 2019·Natural Product Reports·Kuan Zheng, Ran Hong
Jul 5, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jeyun JoHwayoung Yun
Mar 11, 2021·Chemical Communications : Chem Comm·Debobrata PaulRajib Kumar Goswami
Jul 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Xinhui PanJinhui Wang
Dec 5, 2020·ACS Central Science·Iakovos SaridakisNuno Maulide
Aug 25, 2021·Chemistry : a European Journal·Simon HilkerJan-E Bäckvall

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