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Synthesis of (−)-(1S,5R)- and (+)-(1R,5S)-trifluoroanalogues of frontalin

✍ Scribed by Pierfrancesco Bravo; Elonora Corradi; Massimo Frigerio; Stefano Valdo Meille; Walter Panzeri; Cristina Pesenti; Fiorenza Viani

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
209 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

The synthesis of enantiomerically pure (-)-(1S,5R)-1-trifluoromethyl frontalin 7 starting from (-)-(1R)-menthyl (S)-toluene-4-sulfinate, 5-pentenylmagnesium bromide and methyl trifluoroacetate is described. The synthetic procedures to obtain the enantiomer (+)-(1R,5S)-7 are also mentioned. Absolute stereochemistry was unambiguously assigned by X-ray analysis of intermediates 3 and 5.

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