Dichloromethylenation of sugar γ-lactones: a stereospecific synthesis ofL-(+)-muscarine andL-(+)-epimuscarine toluene-p-sulphonates
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 661-664
- https://doi.org/10.1039/p19870000661
Abstract
Treatment of di-isopropylidene-D-mannono-1,4-lactone (3) with hexamethylphosphorous triamide–tetrachioromethane gave the dichloro-olefin (4), which was converted into the ketone (5) by treatment with lithium di-isopropylamide. Reduction with Raney nickel gave the key intermediate (7) together with its isomer (6)(9:1 ratio). Compound (7) was transformed into L-(+)-epimuscarine (2)via glycol cleavage, reduction, tosylation, and treatment with trimethylamine. L-(+)-Muscarine (1) was synthesised from compound (7) by inversion of the hydroxy group configuration at C-3 followed by the above sequence.This publication has 3 references indexed in Scilit:
- Une nouvelle synthese totale de la L(+) et de la D(-)-muscarineTetrahedron, 1985
- Stereospecific synthesis of muscarines and allomuscarines in D- and L-seriesThe Journal of Organic Chemistry, 1982
- A stereospecific synthesis of (+)-muscarineJournal of the Chemical Society, Perkin Transactions 1, 1982