Synthesis of novel alkaloid derivatives from the vinyl ether of lupinine and PH-compounds

被引：16

作者：

Gusarova, Nina K. ^{[1
]}

Malysheva, Svetlana F. ^{[1
]}

Oparina, Ludmila A. ^{[1
]}

Belogorlova, Nataliya A. ^{[1
]}

Tantsyrev, Anatolii P. ^{[1
]}

Parshina, Lidiya N. ^{[1
]}

Sukhov, Boris G. ^{[1
]}

Tlegenov, Rustam T. ^{[2
]}

Trofimova, Boris A. ^{[1
]}

机构：

[1] Russian Acad Sci, Siberian Branch, AE Favorsky Irkutsk Inst Chem, 1 Favorsky St, Irkutsk 664033, Russia

[2] Karakalpakstan State Univ, Nukus 742012, Karakalpak Repu, Uzbekistan

来源：

ARKIVOC | 2009年

基金：

俄罗斯基础研究基金会;

关键词：

Vinyl ether of lupinine; secondary phosphines and phosphine chalcogenides; radical addition; functional quinolizidine alkaloids; PHOSPHINE; ANALOGS;

D O I：

10.3998/ark.5550190.0010.725

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new family of functional quinolizidine alkaloids containing alkoxy groups and phosphine or phosphine chalcogenide fragments has been prepared from the vinyl ether of enantiomerically pure lupinine, secondary phosphines and phosphine sulfide. The reaction proceeds readily under radical initiation to give anti-Markovnikov adducts, dialkyl[2-(octahydro-2H-quinolizin-1-ylmethyloxy) ethyl] phosphines and -phosphine sulfide, in high yields (89-96%). The phosphine moieties of the alkaloids synthesized have been oxidized with air, elemental sulfur or selenium to afford the corresponding phosphine chalcogenides.

引用

页码：260 / 267

页数：8

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