1. Divergent synthesis of two novel muscarine analogues from D-glucose
- Author
-
Ljubica Radić, Mirjana Popsavin, Velimir Popsavin, Vera Ćirin-Novta, and Ostoja Berić
- Subjects
Muscarine ,Stereochemistry ,Organic Chemistry ,Regioselectivity ,Epoxide ,Ring (chemistry) ,Biochemistry ,Combinatorial chemistry ,chemistry.chemical_compound ,chemistry ,D-Glucose ,Drug Discovery ,Muscarinic acetylcholine receptor ,Divergent synthesis - Abstract
A divergent synthesis of two new muscarine analogues bearing the (5 S )-dioxolanyl 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 LiAlH 4 , whereby the natural stereochemistry of (+)-muscarine ( 1 ) and (−)- allo -muscarine ( 2 ) was efficiently established.
- Published
- 1999