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Synthesis 1997; 1997(10): 1128-1130
DOI: 10.1055/s-1997-1323
short paper
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A Facile and Efficient Synthesis of (+)- and (-)-allo-Muscarine and Analogs

Jens Chr. Norrild* , Christian Pedersen
  • *Department of Organic Chemistry, The Technical University of Denmark, DK-2800 Lyngby, Denmark, Fax +33(47)6514382; E-mail: Jens.Norrild@ujf-grenoble.fr
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Publication Date:
31 December 2000 (online)

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Treatment of easily obtainable 1-alkylamino-1,3,6-trideoxyhexitols with hydrogen fluoride in the presence of formic acid gives the corresponding C-5 inverted 2,5-anhydrides in high yields. The synthesis of allo-muscarine and its N-benzyl analog from galactono-1,4-lactone is reported in 30 and 41% overall yield, respectively.

muscarines - tetrahydrofurans - aminodeoxyalditols - hydrogen fluoride

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