E,E-乙烯基烯酮硅基N,O-乙缩醛的立体选择性酰化及其在卡弗瑞芬合成中的应用。

Stereoselective acylation of the E,E-vinylketene silyl N,O-acetal and its application to the synthesis of khafrefungin.

作者信息

Takahashi Yuta, Otsuka Maiko, Harachi Mio, Mukaeda Yuki, Hosokawa Seijiro

机构信息

Department of Applied Chemistry, Faculty of Science and Engineering, Waseda University , 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan.

出版信息

Org Lett. 2014 Aug 15;16(16):4106-9. doi: 10.1021/ol501805j. Epub 2014 Jul 29.

DOI:10.1021/ol501805j

PMID:25072267

Abstract

Stereoselective acylation of the E,E-vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved by using acid anhydrides and SnCl4. Acid anhydrides having alkyl chains gave the adducts in excellent stereoselectivity. The formal synthesis of khafrefungin has been accomplished by the methodology.

摘要

通过使用酸酐和四氯化锡，实现了对具有手性助剂的E,E-乙烯基烯酮硅基N,O-乙缩醛的立体选择性酰化反应。具有烷基链的酸酐以优异的立体选择性得到加合物。已通过该方法完成了卡弗雷菌素的形式合成。