SYNTHESIS OF OXAZATWISTANES AND THEIR HOMO-ANALOGS AND BISHOMO-ANALOGS FROM QUINIDINE - MEDIUM RING-SYSTEMS DERIVED FROM CINCHONA ALKALOIDS

Authors
BRAJE W FRACKENPOHL J LANGER P HOFFMANN HMR
Citation
W. Braje et al., SYNTHESIS OF OXAZATWISTANES AND THEIR HOMO-ANALOGS AND BISHOMO-ANALOGS FROM QUINIDINE - MEDIUM RING-SYSTEMS DERIVED FROM CINCHONA ALKALOIDS, Tetrahedron, 54(14), 1998, pp. 3495-3512
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
14
Year of publication
1998
Pages
3495 - 3512
Database
ISI
SICI code
0040-4020(1998)54:14<3495:SOOATH>2.0.ZU;2-2
Abstract
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 fram ework. TIPS-triflate mediated cyclization of hydroxyaldehydes 13a and 15b to silylated tricyclic hemiacetals 14 and 16 is superior to an int ramolecular S(N)2-approach, especially for the formation of 7- and 8-m embered rings. (C) 1998 Elsevier Science Ltd. All rights reserved.