STEREOSPECIFIC SYNTHESIS OF (-MUSCARINE FROM D-GLUCOSE, SUITABLE FOR PREPARATION OF 5-SUBSTITUTED ANALOGS())

Authors
POPSAVIN V BERIC O RADIC L POPSAVIN M CIRINNOVTA V MILJKOVIC D
Citation
V. Popsavin et al., STEREOSPECIFIC SYNTHESIS OF (-MUSCARINE FROM D-GLUCOSE, SUITABLE FOR PREPARATION OF 5-SUBSTITUTED ANALOGS()), Collection of Czechoslovak Chemical Communications, 63(10), 1998, pp. 1522-1527
Citations number
14
Categorie Soggetti
Chemistry
Journal title
Collection of Czechoslovak Chemical Communications → ACNP
ISSN journal
00100765
Volume
63
Issue
10
Year of publication
1998
Pages
1522 - 1527
Database
ISI
SICI code
0010-0765(1998)63:10<1522:SSO(FD>2.0.ZU;2-5
Abstract
A stereospecific synthesis of (+)-muscarine iodide (1) has been achiev ed starting from D-glucose as a chiral precursor. The key steps of the synthesis involved a stereospecific cyclization of 3,5-di-O-mesyl der ivative 3 into the 2,5-anhydride 4, the stereospecific catalytic hydro genation of unsaturated derivative 6, and the C-4 epimerization of alc ohol 12 by Mitsunobu reaction.