Protoberberines from Reissert-compounds .5. Synthesis of (+/-)-bharatamine

被引：8

作者：

Reimann, E ^{[1
]}

Renz, H ^{[1
]}

Dammertz, W ^{[1
]}

Scholz, T ^{[1
]}

机构：

[1] FACHHSCH ISNY,D-88316 ISNY,GERMANY

来源：

MONATSHEFTE FUR CHEMIE | 1996年 / 127卷 / 02期

关键词：

Reissert compound; intramolecular cyclization; 2-benzyloxy-3-methoxy-8H-dibenzo-[a; g]-8-quinolizinone; (+/-)-bharatamine;

D O I：

10.1007/BF00807398

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Alkylation of the Reissert compound 1 by methyl 2-bromomethylbenzoate (2) followed by spontaneous intramolecular cyclization affords dibenzo[a, g]quinolizinone 4 which in turn can be reduced to benzyl ether 5 by LiAlH4/NaBH4. Debenzylation of 5 by ethanolic HCl furnishes the title compound 6 in improved total yield.

引用

页码：173 / 176

页数：4

共 10 条

[1]

MEISE W, 1971, ARCHIV PHARM BERICHT, V304, P182, DOI 10.1002/ardp.19713040305

[2]

PAKRASHI SC, 1985, J INDIAN CHEM SOC, V62, P1003

[3] STUDIES ON INDIAN MEDICINAL-PLANTS .71. BHARATAMINE - A UNIQUE PROTOBERBERINE ALKALOID FROM ALANGIUM-LAMARCKII THW, BIOGENETICALLY DERIVED FROM MONOTERPENOID PRECURSOR [J].