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Synthesis and conformational analysis of a chiral fluorinated bilirubin analog lacking carboxyl groups

✍ Scribed by Stefan E. Boiadjiev; David A. Lightner

Publisher
Journal of Heterocyclic Chemistry
Year
1999
Tongue
English
Weight
629 KB
Volume
36
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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.

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