Synthesis of oxazatwistanes and their homo- and bishomo-analogues from quinidine - Medium ring systems derived from cinchona alkaloids

被引：46

作者：

Braje, W ^{[1
]}

Frackenpohl, J ^{[1
]}

Langer, P ^{[1
]}

Hoffmann, HMR ^{[1
]}

机构：

[1] Univ Hannover, Dept Organ Chem, D-30167 Hannover, Germany

来源：

TETRAHEDRON | 1998年 / 54卷 / 14期

关键词：

D O I：

10.1016/S0040-4020(98)00085-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Suitable functionalization of the vinyl group of quinidine (la) allows cyclization involving the C9 hydroxyl group, giving novel 6-, 7- and 8-membered rings containing a distorted 1-azabicyclo[2.2.2]octane framework. TIPS-triflate mediated cyclization of hydroxyaldehydes 13a and 15b to silylated tricyclic hemiacetals 14 and 16 is superior to an intramolecular S(N)2-approach, especially for the formation of 7- and 8-membered rings. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3495 / 3512

页数：18

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