期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 4, 页码 1087-1091出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201609941
关键词
alkaloids; diastereoselectivity; radical cyclization; spiro compounds; total synthesis
资金
- Cabinet Office, Government of Japan through Funding Program for Next-Generation World-Leading Researchers [LS008]
- JSPS KAKENHI [JP16H01127, JP16H00999, 26253001]
- Grants-in-Aid for Scientific Research [25102007, 16H01147, 25102001, 16H00999, 16H05073, 26253001, 16H01127] Funding Source: KAKEN
Stereoselective total syntheses of (-)-histrionicotoxin and (-)-histrionicotoxin 235A are described. The 1-azaspiro[5.5]undecane skeleton was constructed diastereoselectively by a radical translocation-cyclization reaction involving a chiral cyclic acetal; the use of tris( trimethylsilyl) silane was crucial for the high diastereoselectivity. The cyclization product was converted into (-)-histrionicotoxin 235A through a one-pot partial-reduction-allylation reaction of a derivative containing an unprotected lactam. Finally, two terminal alkenes were transformed into enynes with the 1,3-amino alcohol protected as an oxathiazolidine oxide to complete the total synthesis of (-)-histrionicotoxin.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据