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

Authors
Bravo, P Corradi, E Frigerio, M Meille, SV Panzeri, W Pesenti, C Viani, F
Citation
P. Bravo et al., Synthesis of (-)-(1S,5R)- and (+)-(1R,5S)-trifluoroanalogues of frontalin, TETRAHEDR L, 40(34), 1999, pp. 6317-6320
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
34
Year of publication
1999
Pages
6317 - 6320
Database
ISI
SICI code
0040-4039(19990820)40:34<6317:SO(A(O>2.0.ZU;2-E
Abstract
The synthesis of enantiomerically pure (-)-(1S,5R)-1-trifluoromethyl fronta lin 7 starting from (-)-(1R)-menthyl (S)-toluene-4-sulfinate, 5-pentenylmag nesium bromide and methyl trifluoroacetate is described. The synthetic proc edures to obtain the enantiomer (+)-(1R,5S)-7 are also mentioned. Absolute stereochemistry was unambiguously assigned by X-ray analysis of intermediat es 3 and 5. (C) 1999 Elsevier Science Ltd. All rights reserved.