Synthesis and NMR assignment of pentacycloundecane precursors of potential pharmaceutical agents.
The synthesis and complete NMR elucidation of eight novel pentacycloundecane (PCU) derivatives are reported. These compounds are precursors in the synthesis of PCU-based anti-tuberculosis (TB) agents and potential human immunodeficiency virus (HIV) protease inhibitors. Two-dimensional (2D) NMR techniques were used to assign the NMR spectra for these compounds. Substitution of the cage molecule at (C-8/11) further complicates the assignment, since some of the substituted alkyl chain groups overlap with the cage proton signals. The side chain heteroatoms also introduce a rare through-space deshielding effect to some of the carbon atoms of the cage skeleton. Ring strain in the rigid cage skeleton appears to induce drastic electronic changes in some parts of the cage framework. This observation is more dramatic for the C-4 methylene group of the cage diols and the cage ethers.
Onajole
Oluseye K
OK
School of Chemistry, University of KwaZulu-Natal, Durban, South Africa.
Makatini
Maya M
MM
Govender
Patrick
P
Govender
Thavendran
T
Maguire
Glenn E M
GE
Kruger
Hendrik G
HG
D000995:Antitubercular Agents / Q000138:chemical synthesis / Q000737:chemistry*; D003198:Computer Simulation; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000592:standards; D008956:Models, Chemical; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D012015:Reference Standards; D013237:Stereoisomerism
D000995:Antitubercular Agents; D017320:HIV Protease Inhibitors; D011083:Polycyclic Compounds