Synthesis and Conformational Analysis of a Chiral Fluorinate Bilirubin Analog Lacking Carboxyl Groups

摘要

An optically active analog 1 of etiobilirubin-IV#gamma# with a single fluorine on each of the C(8) and C(12) alkyl groups has been synthesized in order to examine its potential for hydrogen bonding with fluorine. Circular dichroism spectroscopy reveals an unusually strong influence of 2,2,2-trifluoroethanol solvent on diastereo-selection of the M-helical conformation of (8~1S,12~1S)-1.