Biosynthesis of naphthylisoquinoline alkaloids: synthesis and incorporation of an advanced 13C 2-labeled isoquinoline precursor

Biosynthetic studies on naphthylisoquinoline alkaloids involving a specifically [1,1′- 13C 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 meth...

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Bibliographic Details
Published inTetrahedron Vol. 63; no. 8; pp. 1755 - 1761
Main Authors Bringmann, Gerhard, Mutanyatta-Comar, Joan, Greb, Marco, Rüdenauer, Stefan, Noll, Torsten F., Irmer, Andreas
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 2007
Subjects
13C 2 labeling
Biosynthesis
Dioncophylline A
Naphthylisoquinoline alkaloids
Triphyophyllum peltatum
Dioncophylline A
Triphyophyllum peltatum
Biosynthesis
Naphthylisoquinoline alkaloids
13C 2 labeling
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Summary:Biosynthetic studies on naphthylisoquinoline alkaloids involving a specifically [1,1′- 13C 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 ( 1H, 13C 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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2006.12.022