Year
2001
Degree Name
Master of Science (Hons.)
Department
Faculty of Science
Recommended Citation
Sengpracha, Waya, Synthesis of tribulusterine, a potent toxic alkaloid from Tribulus terrestris, Master of Science (Hons.) thesis, Faculty of Science, University of Wollongong, 2001. https://ro.uow.edu.au/theses/2883
Abstract
Synthetic approaches to tribulusterine (15), a suspected toxic alkaloid from Tribulus terrestris, have been investigated via nucleophilic and electrophilic substitution reactions, and the Pictet-Spengler cyclisation reaction. Nucleophilic substitution reactions of the 9-(N,A^-dimethylsulfamoyl)-p-carboline-A^-oxide (50) with the furyllithium (46a) yielded the new 1-substituted P-carboline, l-(3- furyl)methoxy-9-(A^,A/'-dimethylsulfamoyl)-(3-carboline (52). Bromination of the Pcarboline derivative (51) afforded 1,3,6,8-tetrabromo-P-carboline and 3,6,8-tribromop- carboline as major products when the lithiated P-carboline (51) was treated with Nbromosuccinimide (NBS) and bromine, respectively. The Pictet-Spengler reaction approach may have yielded the required alkaloid, tribulusterine (15), based on some spectroscopic evidence. The new furan derivative, 3-(hydroxymethyl)-2-furaldehyde (66), required for the Pictet-Spengler approach, was synthesised via a lithiationmediated procedure. A precursor (33) for a palladium-catalysed Negishi-type crosscoupling approach was also prepared.
Unless otherwise indicated, the views expressed in this thesis are those of the author and do not necessarily represent the views of the University of Wollongong.