（-）-网抑素及其三种立体异构体的氟代混合物合成

Fluorous mixture synthesis of (-)-dictyostatin and three stereoisomers.

作者信息

Fukui Yoshikazu, Brückner Arndt M, Shin Youseung, Balachandran Raghavan, Day Billy W, Curran Dennis P

机构信息

Department of Chemistry, University of Pittsburgh, Pennsylvania 15260, USA.

出版信息

Org Lett. 2006 Jan 19;8(2):301-4. doi: 10.1021/ol0526827.

DOI:10.1021/ol0526827

PMID:16408900

Abstract

[reaction: see text] A mixture of four stereoisomers whose configurations are encoded by fluorous silyl protecting groups has been prepared and converted over 22 steps to a mixture of protected dictyostatins. Demixing by fluorous HPLC followed by removal of the fluorous protecting groups (detagging) provides dictyostatin and three C6,C7 stereoisomers. Biological evaluation showed that the monoepimers of the natural product retained highly potent activity.

摘要

[反应：见正文] 已制备出一种由氟代甲硅烷基保护基团编码其构型的四种立体异构体的混合物，并通过22步反应将其转化为受保护的网抑素混合物。通过氟代高效液相色谱法进行分离，随后除去氟代保护基团（脱标签），得到网抑素和三种C6、C7立体异构体。生物学评估表明，天然产物的单差向异构体保留了高效活性。