6533b827fe1ef96bd1286d8e

RESEARCH PRODUCT

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

Arto ValkonenJuha KoivukorpiErkki Kolehmainen

subject

Lithocholic acidMolecular massChemical shiftOrganic ChemistryAb initioCarbon-13 NMRMedicinal chemistryAnalytical ChemistryInorganic ChemistryNMR spectra databasechemistry.chemical_compoundchemistryMass spectrumOrganic chemistrySpectroscopyPyrrole

description

Abstract 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 1 H, 13 C, PFG DQF 1 H– 1 H COSY, 1 H– 1 H ROESY, 13 C DEPT-135, PFG 1 H– 13 C HMQC, PFG 1 H– 13 C HMBC, and PFG 1 H– 15 N 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 13 C 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.

yearjournalcountryeditionlanguage
2004-05-01Journal of Molecular Structure
https://doi.org/10.1016/j.molstruc.2004.02.014