SYNTHESIS OF (3S,5S)-QUINUCLIDINE-3,5-DIOL AND OF -ALPHA,7A-ALPHA)]-OCTAHYDRO-2-FURO[2,3-C]PYRIDINOL FROM D-ARABINOSE

Authors
VAZQUEZTATO MP SEIJAS JA FLEET GWJ MATHEWS CJ HEMMINGS PR BROWN D
Citation
Mp. Vazqueztato et al., SYNTHESIS OF (3S,5S)-QUINUCLIDINE-3,5-DIOL AND OF -ALPHA,7A-ALPHA)]-OCTAHYDRO-2-FURO[2,3-C]PYRIDINOL FROM D-ARABINOSE, Tetrahedron, 51(3), 1995, pp. 959-974
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
3
Year of publication
1995
Pages
959 - 974
Database
ISI
SICI code
0040-4020(1995)51:3<959:SO(AO->2.0.ZU;2-B
Abstract
The synthesis of (3S,5S)-quinuclidine-3,5-diol is achieved by an intro duction of a 2 carbon chain at C-3 of D-arabinose, followed by joining the terminus of the chain extension to C-1 and C-5 of the sugar, the synthesis of [3S-(3 alpha,3a alpha,7a alpha)]-octahydro-2-furo[2,3-c]p yridinol, a potential muscarine mimic, is described.