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Synthesis of Aristotelia ‐Type Alkaloids. Part III. (3 R ,4 R )‐ and (3 R ,4 S )‐1‐ p ‐menthene‐3,8‐diol and the corresponding racemates: Preparation and assignment of configuration
Author(s) -
Burkard Stefan,
Looser Martin,
Borschberg HansJürg
Publication year - 1988
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19880710122
Subject(s) - chemistry , absolute configuration , diol , resolution (logic) , optically active , stereochemistry , organic chemistry , artificial intelligence , computer science
A 1:1 mixture of the racemic trans ‐ and cis ‐1‐ p ‐menthene‐3,8‐diols ((±)‐ 3 and (±)‐ 4 , resp.) was readily prepared in 3 steps starting from 3‐methyl‐2‐cyclohexen‐1‐one. The relative configuration of the diols, purified via the corresponding cyclocarbonates, was assigned by 1 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 )‐1‐phenylethylamine. The absolute configuration of the resulting diols was determined by chemical correlation with standards of known absolute configuration.