A facile method for the synthesis of glaucine and norglaucine from boldine

被引：24

作者：

Huang, WJ ^{[1
]}

Chen, CH ^{[1
]}

Singh, OV ^{[1
]}

Lee, SL ^{[1
]}

Lee, SS ^{[1
]}

机构：

[1] Natl Taiwan Univ, Coll Med, Sch Pharm, Taipei 100, Taiwan

来源：

SYNTHETIC COMMUNICATIONS | 2002年 / 32卷 / 23期

关键词：

glaucine; norglaucine; large-scale preparation;

D O I：

10.1081/SCC-120014988

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A large-scale preparation of glaucine was achieved by reacting boldine with trimethylphenylammonium chloride and potassium t-butoxide in high yield. Treatment of glaucine with 30% H2O2, subsequent with hydrated ferrous sulfate, afforded norglaucine in an overall yield of 40%.

引用

页码：3681 / 3686

页数：6

共 15 条

[1]

ADAMS R, 1953, ORGANIC REACTIONS ED, V7, P198

[2] THE BIOSYNTHESIS OF GLAUCINE IN LITSEA-GLUTINOSA [J].

BHAKUNI, DS ;

JAIN, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (06) :1447-1449

[3]

BREMNER JB, 1978, AUS J CHEM, V313, P317

[4] CONVERSION OF APORPHINES INTO N-NORAPORPHINE ALKALOIDS [J].

CAVA, MP ;

SRINIVASAN, M .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (02) :330-+

[5] Chiral auxiliary mediated Pictet-Spengler reactions - Asymmetric syntheses of (-)-laudanosine, (+)-glaucine and (-)-xylopinine. [J].

Comins, DL ;

Thakker, PM ;

Baevsky, MF ;

Badawi, MM .

TETRAHEDRON, 1997, 53 (48) :16327-16340

[6] Bronchodilator and anti-inflammatory activities of glaucine:: In vitro studies in human airway smooth muscle and polymorphonuclear leukocytes [J].

Cortijo, J ;

Villagrasa, V ;

Pons, R ;

Berto, L ;

Martí-Cabrera, M ;

Martinez-Losa, M ;

Domenech, T ;

Beleta, J ;

Morcillo, EJ .

BRITISH JOURNAL OF PHARMACOLOGY, 1999, 127 (07) :1641-1651

[7]

FALTIS K, 1921, MONATSH CHEM, V42, P379

[8] AN ASYMMETRIC-SYNTHESIS OF APORPHINE AND RELATED ALKALOIDS VIA CHIRAL FORMAMIDINES - (+)-GLAUCINE, (+)-HOMOGLAUCINE, AND (-)-8,9-DIDEMETHOXYTHALISOPAVINE [J].

GOTTLIEB, L ;

MEYERS, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (21) :5659-5662

[9]

LU ST, 1985, HETEROCYCLES, V238, P3085

[10] A NEW REAGENT FOR THE SELECTIVE, HIGH-YIELD N-DEALKYLATION OF TERTIARY-AMINES - IMPROVED SYNTHESES OF NALTREXONE AND NALBUPHINE [J].

OLOFSON, RA ;

MARTZ, JT ;

SENET, JP ;

PITEAU, M ;

MALFROOT, T .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (11) :2081-2082

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