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Issue 0, 1982
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A stereospecific synthesis of (+)-muscarine

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.

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Article type: Paper
DOI: 10.1039/P19820000809
Citation: J. Chem. Soc., Perkin Trans. 1, 1982,0, 809-813
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    A stereospecific synthesis of (+)-muscarine

    A. M. Mubarak and D. M. Brown, J. Chem. Soc., Perkin Trans. 1, 1982, 0, 809
    DOI: 10.1039/P19820000809

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