Synthesis and characterization of lithocholic acid derived dipyrromethanes: precursors for pyrrole-steroidal macrocycles

Three steroidal dipyrromethanes, 3,3,24,24-tetrakis(pyrrol-2-yl)-5β-cholane 1, 3,3-bis(pyrrol-2-yl)-5β-cholan-24-oic acid 2, and methyl 3,3-bis(pyrrol-2-yl)-5β-cholan-24-oate 3, have been prepared from 3α-hydroxy-5β-cholan-24-oic acid (lithocholic acid) 4 in good overall yields. The structures of 1–...

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Bibliographic Details
Published in:Journal of molecular structure 2004-05, Vol.693 (1), p.81-86
Main Authors: Koivukorpi, Juha, Valkonen, Arto, Kolehmainen, Erkki
Format: Article
Language:English
Subjects:
Dipyrromethane
Electrospray ionization and EI mass spectra
Lithocholic acid
Multinuclear magnetic resonance
Pyrrole
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Summary:Three steroidal dipyrromethanes, 3,3,24,24-tetrakis(pyrrol-2-yl)-5β-cholane 1, 3,3-bis(pyrrol-2-yl)-5β-cholan-24-oic acid 2, and methyl 3,3-bis(pyrrol-2-yl)-5β-cholan-24-oate 3, have been prepared from 3α-hydroxy-5β-cholan-24-oic acid (lithocholic acid) 4 in good overall yields. The structures of 1– 3 have been fully characterized by 1H, 13C, PFG DQF 1H– 1H COSY, 1H– 1H ROESY, 13C DEPT-135, PFG 1H– 13C HMQC, PFG 1H– 13C HMBC, and PFG 1H– 15N HMBC NMR spectra. Their molecular weights and compositions have been determined by ESI-TOF and EI mass spectra, and elemental analyses. The energetically optimised geometry and isotropic 13C NMR chemical shifts of 3,3,24,24-tetrakis(pyrrol-2-yl)-5β-cholane 1 have been calculated by ab initio HF/6-31G* and DFT B3PW91/6-311G* methods.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2004.02.014