title: Synthesis, chromatographic separation, vibrational circular dichroism spectroscopy, and ab initio DFT studies of chiral thiepane tetraol derivatives.
abstract: Optically pure enantiomers of the chiral tetrahydroxythiepane derivative 3,6-dihydroxy-4,5-O-isopropylidene-thiepane (3) are obtained using a novel protocol in which a library of all possible stereoisomers of 3 is synthesized, followed by two-step stereoselective chromatography, using, first, conventional achiral and, then, chiral stationary phases. Configurational and conformational analysis of 3 are carried out using Vibrational Circular Dichroism (VCD) spectroscopy in conjunction with ab initio DFT calculations. The absolute configuration of 3 is shown to be 3R,4S,5R,6R-(+)/3S,4R,5S,6S-(-).
authors.affiliation: Department of Organic Chemistry "A. Mangini", University of Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy. cere@ms.fci.unibo.it
authors.forename: Vanda
authors.initials: V
authors.lastname: Cerè
authors.forename: Francesca
authors.initials: F
authors.lastname: Peri
authors.forename: Salvatore
authors.initials: S
authors.lastname: Pollicino
authors.forename: Alfredo
authors.initials: A
authors.lastname: Ricci
authors.forename: Frank J
authors.initials: FJ
authors.lastname: Devlin
authors.forename: Philip J
authors.initials: PJ
authors.lastname: Stephens
authors.forename: Francesco
authors.initials: F
authors.lastname: Gasparrini
authors.forename: Romina
authors.initials: R
authors.lastname: Rompietti
authors.forename: Claudio
authors.initials: C
authors.lastname: Villani