HEXACYCLIC INDOLE ALKALOIDS - A HIGHLY CONVERGENT TOTAL SYNTHESIS OF CUANZINE

被引：13

作者：

PALMISANO, G ^{[1
]}

DANIELI, B ^{[1
]}

LESMA, G ^{[1
]}

PASSARELLA, D ^{[1
]}

TOMA, L ^{[1
]}

机构：

[1] UNIV PAVIA,DIPARTMENTO CHIM ORGAN,I-27100 PAVIA,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 07期

关键词：

D O I：

10.1021/jo00007a024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel route to the hexacyclic indole alkaloid cuanzine 1 has been developed. Key synthetic steps include the cyclocondensation of the imine 8 with the dihydrofuran 10 followed by homogeneous-catalyzed hydrogenation, wherein the COOMe group at C(20) serves as a diastereocontrol element in establishing the C(15) stereogenicity. In order to define local energy minima, the conformational space of some intermediates has been explored by empirical force field calculations (MM2).

引用

页码：2380 / 2386

页数：7