A stereospecific synthesis of (+)-muscarine
- 1 January 1982
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 809-813
- https://doi.org/10.1039/p19820000809
Abstract
A stereospecific synthesis of (+)-muscarine (1) is described in which acid-catalysed cyclisation of D-mannitol gives 2,5-anhydro-D-glucitol, isolated as its 1,3-O-isopropylidene-4,6-dibenzoate (3); acid hydrolysis then tosylation gives the 1,3-di-O-tosyl derivative (7), converted by sodium methoxide–methanol into 2,5:3,4-dianhydro–1-tosyl-D-allitol (8). This epoxide with sodium bis-(2-methoxyethoxy)aluminium hydride gives 2,5-anhydro-1,4-dideoxy-D-ribo-hexitol (10) and its 1,3-dideoxy-isomer (11)(12:1). The former, with tosyl chloride then trimethylamine gives (+)-muscarine tosylate, also isolated as chloride and bromide salts.This publication has 0 references indexed in Scilit: