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Synthesis and conformational analysis of a chiral fluorinated bilirubin analog lacking carboxyl groups
Author(s) -
Boiadjiev Stefan E.,
Lightner David A.
Publication year - 1999
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570360424
Subject(s) - chemistry , circular dichroism , alkyl , fluorine , hydrogen bond , solvent , optically active , stereochemistry , crystallography , organic chemistry , molecule
An optically active analog 1 of etiobilirubin‐IVγ 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 1 S ,12 1 S )‐1.