Synthesis of 2,6-disubstituted piperidine alkaloids from ladybird beetles Calvia 10-guttata and Calvia 14-guttata

被引：22

作者：

Kubizna, Peter ^{[1
]}

Spanik, Ivan ^{[2
]}

Kozisek, Jozef ^{[3
]}

Szolcsanyi, Peter ^{[1
]}

机构：

[1] Slovak Univ Technol Bratislava, Dept Organ Chem, SK-81237 Bratislava, Slovakia

[2] Slovak Univ Technol Bratislava, Dept Analyt Chem, SK-81237 Bratislava, Slovakia

[3] Slovak Univ Technol Bratislava, Dept Phys Chem, SK-81237 Bratislava, Slovakia

来源：

TETRAHEDRON | 2010年 / 66卷 / 13期

关键词：

Palladium; Carbonylation; Amino alcohols; Heterogeneous catalysis; Natural products; POTENTIAL GLYCOSIDASE INHIBITORS; O-CENTERED NUCLEOPHILES; DOUBLE-BOND GEOMETRY; INTRAMOLECULAR AMINOCARBONYLATION; TETHERED ACRYLATES; TERMINAL EPOXIDES; MICHAEL ADDITION; RESIN GLYCOSIDES; METAL CATALYSIS; C-6; HOMOLOGS;

D O I：

10.1016/j.tet.2010.01.106

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically pure (+)-calvine, (+)-2-epicalvine, (2S,6S)-(6-pentylpiperidin-2-yl)acetic acid methyl ester and (2R,6S)-(6-pentylpiperidin-2-yl)acetic acid methyl ester, four piperidine alkaloids isolated from ladybird beetles of the genus Calvia (Coccinellidae), were synthesised from a common precursor using cyclisative Pd(II)/Cu(II)-catalysed carboamination-(methoxy)carbonylation tandem reaction of alkenylamines as a key step. The first single-crystal X-ray analysis of (+)-calvine confirmed its proposed absolute configuration to be (2S,6S) corresponding to that of natural product. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2351 / 2355

页数：5

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