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.
Synthesis of (-)-(1S,5R)- and (+)-(1R,5S)-trifluoroanalogues of frontalin
Panzeri Walter;
1999
Abstract
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.File in questo prodotto:
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