Synthesis of 2-fluoro analogues of frontalin

Authors
Bravo, P Frigerio, M Ono, T Panzeri, W Pesenti, C Sekine, A Viani, F
Citation
P. Bravo et al., Synthesis of 2-fluoro analogues of frontalin, EUR J ORG C, (8), 2000, pp. 1387-1389
Citations number
12
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
8
Year of publication
2000
Pages
1387 - 1389
Database
ISI
SICI code
1434-193X(200004):8<1387:SO2AOF>2.0.ZU;2-B
Abstract
The synthesis of enantiomerically and diastereomerically pure (-)-(1R,2R,5R )- and (-)-(1R,2S,5R)-2-fluoro frontalin (7) starting from (+)-(1S)-menthyl -(R)-toluene-4-sulfinate, methylmagnesium bromide, methyl fluoroacetate, 4- pentenyl bromide and diazomethane is described. The absolute stereochemistr y was unambiguously determined by X-ray analysis of (+)-(1S,2R,5S,R-S)-5, a n intermediate in the synthesis of the enantiomeric (+)-(1S,2R,5S)-2-fluoro frontalin (7).