Synthesis of the unusual octahydropyrano[2,3-b]pyridine ring system of ′upenamide

被引：11

作者：

Maia, AA

Mons, S

Gil, RPD

Marazano, C

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

[2] Univ Fed Minas Gerais, Dept Quim, Belo Horizonte, MG, Brazil

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 05期

关键词：

' upenamide; imines; hemiaminal; NMR spectroscopy; alkaloids;

D O I：

10.1002/ejoc.200300708

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe for the first time the preparation of a model octahydropyrano[2,3-b]pyridine 23 bearing substituents at positions 2 and 8, as in the natural alkaloid 'upenamide. The four inseparable diastereoisomers of 23, present in an 81:3:16:trace ratio, were analyzed by NMR spectroscopy experiments to fully determine their relative configurations and conformations. The major diastereoisomer of this non-macrocyclic analog has the same configuration as in natural 'upenamide.(C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

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页码：1057 / 1062

页数：6

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