远程立体诱导分子内腈氧化物环加成反应：(-)-11β-羟基弯孢霉菌素的不对称全合成及结构修正
Remote Stereoinductive Intramolecular Nitrile Oxide Cycloaddition: Asymmetric Total Synthesis and Structure Revision of (-)-11β-Hydroxycurvularin.
作者信息
Choe Hyeonjeong, Pham Thuy Trang, Lee Joo Yun, Latif Muhammad, Park Haeil, Kang Young Kee, Lee Jongkook
机构信息
Drug Discovery Division, Korea Research Institute of Chemical Technology , Yuseong, Daejeon 34114, Republic of Korea.
College of Pharmacy, Kangwon National University , 1 Kangwondaehak-gil, Chuncheon, Gangwon-do 24341, Republic of Korea.
出版信息
J Org Chem. 2016 Mar 18;81(6):2612-7. doi: 10.1021/acs.joc.5b02760. Epub 2016 Feb 29.
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.
完成了具有β - 羟基酮部分的大环内酯（-）-11β - 羟基弯孢霉菌素（1b）的首次全合成及结构修正。该天然产物中的β - 羟基酮部分是通过异恶唑啉环中N - O键的断裂引入的，而异恶唑啉环是通过分子内腈氧化物环加成以1,5 - 远程立体控制方式非对映选择性地形成的。
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