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Synthesis of Aristotelia-Type Alkaloids. Part III. (3R,4R)- and (3R,4S)-1-p-menthene-3,8-diol and the corresponding racemates: Preparation and assignment of configuration

✍ Scribed by Stefan Burkard; Martin Looser; Hans-Jürg Borschberg

Book ID: 102860058
Publisher: John Wiley and Sons
Year: 1988
Tongue: German
Weight: 616 KB
Volume: 71
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19880710122

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✦ Synopsis

A 1:l mixture of the racemic trans-and cis-l-p-menthene-3,8-diols ((+)-3 and (It)-4, resp.) was readily prepared in 3 steps starting from 3-methyl-2-cyclohexen-I-one. The relative configuration of the diols, purified oiu the corresponding cyclocarbonates, was assigned by 'H-NMR spectroscopy and found to be at variance with tentative claims in the literature. Optically active samples of 3 and 4 were prepared by resolution of the racemates with (R)-I-phenylethylamine. The absolute configuration of the resulting diols was determined by chemical correlation with standards of known absolute configuration.

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