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.