A synthesis of (-)-tashiromine and formal synthesis of (+)-tashiromine utilizing a highly enantioselective pyrrole/cobaloxime pi-cation cyclization

被引：43

作者：

Gage, JL ^{[1
]}

Branchard, BP ^{[1
]}

机构：

[1] UNIV OREGON,DEPT CHEM,EUGENE,OR 97403

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 40期

关键词：

D O I：

10.1016/S0040-4039(97)01638-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclization of (5-N-pyrrolyl-2-hydroxypentyl)cobaloxime (13) proceeds by intramolecular electrophilic aromatic substitution of a cobaloxime pi-cation onto the pyrrole ring to provide 6-exo cyclization product (14) in 95% yield. This cyclization is highly enantioselective. It is applied to a synthesis of highly enantioenriched (-)-tashiromine, (-)-21, and a formal synthesis of (+)-tashiromine. (C) 1997 Elsevier Science Ltd.

引用

页码：7007 / 7010

页数：4

共 26 条

[1] THE SYNTHESIS OF INDOLIZIDINE AND QUINOLIZIDINE RING-SYSTEMS BY FREE-RADICAL CYCLIZATION OF 4-AZA-6-METHOXYCARBONYL-5-HEXENYL RADICALS [J].