Biosynthesis of naphthylisoquinoline alkaloids:: synthesis and incorporation of an advanced 13C2-labeled isoquinoline precursor

被引：29

作者：

Bringmann, Gerhard ^{[1
]}

Mutanyatta-Comar, Joan ^{[1
]}

Greb, Marco ^{[1
]}

Rudenauer, Stefan ^{[1
]}

Noll, Torsten F. ^{[1
]}

Irmer, Andreas ^{[1
]}

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

来源：

TETRAHEDRON | 2007年 / 63卷 / 08期

关键词：

naphthylisoquinoline alkaloids; biosynthesis; dioncophylline A; Triphyophyllum peltatum; C-13(2) labeling;

D O I：

10.1016/j.tet.2006.12.022

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Biosynthetic studies on naphthylisoquinoline alkaloids involving a specifically [1,1,-13 C-2]-labeled dihydroisoquinoline 7 are described. The synthesized precursor 7 was fed to callus cultures of Triphyophyllum peltatum and the isolated secondary metabolites were characterized by spectroscopic methods (H-1, C-13 NMR, and INADEQUATE experiments). The unambiguous incorporation of the precursor into dioncophylline A and two minor naphthylisoquinolines, together with the formation of the labeled corresponding trans-configured tetrahydroisoquinoline, proves the implication of such advanced intermediates in the proposed biosynthetic pathway of naphthylisoquinoline alkaloids. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：1755 / 1761

页数：7

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