Divergent synthesis of two novel muscarine analogues from D-glucose

Authors
Popsavin, V Popsavin, M Radic, L Beric, O Cirin-Novta, V
Citation
V. Popsavin et al., Divergent synthesis of two novel muscarine analogues from D-glucose, TETRAHEDR L, 40(52), 1999, pp. 9305-9308
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
52
Year of publication
1999
Pages
9305 - 9308
Database
ISI
SICI code
0040-4039(199912)40:52<9305:DSOTNM>2.0.ZU;2-A
Abstract
A divergent synthesis of two new muscarine analogues bearing the (SS)-dioxo lanyl isosteric group was achieved starting from D-glucose, enabling access to libraries of potential muscarinic agonists or antagonists. The key step of the synthesis involved a regioselective epoxide ring opening in 2,5:3,4 -dianhydro derivatives 5 and 15 with LiAlH4, whereby the natural stereochem istry of (+)-muscarine (1) and (-)-allo-muscarine (2) was efficiently estab lished. (C) 1999 Elsevier Science Ltd. All rights reserved.