Issue 0, 1982

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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1982, 809-813

A stereospecific synthesis of (+)-muscarine

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements