通过二甲基二氧杂环丙烷氧化合成丝裂霉素和FR900482的环系。

Synthesis of the mitomycin and FR900482 ring systems via dimethyldioxirane oxidation.

作者信息

Colandrea Vincent J, Rajaraman Shanthi, Jimenez Leslie S

机构信息

Department of Chemistry & Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, New Jersey 08854-8087, USA.

出版信息

Org Lett. 2003 Mar 20;5(6):785-7. doi: 10.1021/ol026738y.

DOI:10.1021/ol026738y

PMID:12633071

Abstract

[reaction: see text] Dimethyldioxirane oxidizes a 2,3-dihydo-1H-pyrrolo[1,2-a]indole unsubstituted at the C-9 position stereoselectively to form a hydroxy ketone with all the basic elements of the mitomycin ring system. On the other hand, a 2,3-dihydo-1H-pyrrolo[1,2-a]indole derivative substituted with an alkyl group at C-9 undergoes an oxidative ring expansion in the presence of dimethyldioxirane to give an FR900482 analogue.

摘要

[反应：见正文] 二甲基二氧杂环丙烷将在C-9位未被取代的2,3-二氢-1H-吡咯并[1,2-a]吲哚立体选择性地氧化，形成具有丝裂霉素环系所有基本元素的羟基酮。另一方面，在C-9位被烷基取代的2,3-二氢-1H-吡咯并[1,2-a]吲哚衍生物在二甲基二氧杂环丙烷存在下发生氧化扩环反应，生成FR900482类似物。