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TetrahedronVolume 56, Issue 32, 4 August 2000, Pages 5929-5940

A divergent synthesis of (+)-muscarine and (+)-epi-muscarine from D-glucose(Article)

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  • University of Novi Sad, Faculty of Sciences, Institute of Chemistry, Obradovica 3, 21000 Novi Sad

Abstract

A novel stereospecific synthesis of (+)-muscarine and (+)-epi-muscarine has been achieved by utilizing D-glucose as a chiral precursor. The key steps of the synthesis involved stereospecific cyclization of 3,5-di-O-sulfonyl-D-glucofuranose derivatives into the corresponding 2,5-anhydrides, and stereospecific hydrogenation of 2,5-anhydro-L-threo-hex-2-enose ethylene acetal derivatives, thus providing an access to divergent intermediates for the preparation of both target molecules in a fully stereospecific manner. (C) 2000 Elsevier Science Ltd.

Author keywords

(+)-Epi-muscarine(+)-Muscarine2,5-anhydro sugarsD-glucoseStereospecific synthesis

Indexed keywords

EMTREE drug terms:alkaloidglucosemuscarine
EMTREE medical terms:articlecarbon nuclear magnetic resonancecyclizationdrug structuredrug synthesishydrogenationnonhumanpriority journalproton nuclear magnetic resonancestereochemistry

Chemicals and CAS Registry Numbers:

glucose, 50-99-7, 84778-64-3; muscarine, 300-54-9

Funding details

  • 1

    This work was supported by a research grant from the Ministry of Science and Technology of the Republic of Serbia. The authors thank Dr P. Radivojša (Centre of Chemistry, ICTM, Belgrade, YU), for the measurements of optical rotation, as well as to Mrs T. Marinko-Covell (University of Leeds, UK) and to Mr D. Djoković (Faculty of Chemistry, University of Belgrade, YU), for recording the mass spectra.

  • ISSN: 00404020
  • CODEN: TETRA
  • Source Type: Journal
  • Original language: English
  • DOI: 10.1016/S0040-4020(00)00482-8
  • Document Type: Article
  • Publisher: Elsevier Ltd

  Popsavin, V.; University of Novi Sad, Faculty of Sciences, Institute of Chemistry, Trg D. Obradovica 3, ;
© Copyright 2017 Elsevier B.V., All rights reserved.

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