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
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.
引用
收藏
页码:1057 / 1062
页数:6
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