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A simple, stereospecific synthesis of DL-muscarine and DL-allomuscarine

✍ Scribed by Takeshi Matsumoto; Akitami Ichihara; Noriki Itŏ

Publisher: Elsevier Science
Year: 1968
Tongue: French
Weight: 151 KB
Volume: 9
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)99072-0

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✦ Synopsis

In the previous papers 1)2) concerning the synthesis of muscarines, we reported a partially stereospecific synthesis in which the hydroxyl group of a diacid (I) was introduced selectively in trans manner to the methyl group.

Decarboxylation of I, however , proceeded non-stereoselectively giving a mixture of two stereoisomeric monocarboxylic acids, IIa and IIb in a ratio of 1:l.

The two acids (IIa, IIb) were converted to dl-muscarine'(II1) and dl-allomuscarine (IV) respectively.

Present communication describes a simple, fully stereospecific synthesis of muscarines starting from the bromolactone amide (V) obtained earlier 1)2) as

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