Total synthesis of the putative structure of nagelamide D.
A total synthesis of the putative structure of nagelamide D from imidazole is described. A Stille cross-coupling is used to construct the bis imidazole skeleton, and the pyrrolecarboxamides are introduced via a double Mitsunobu reaction using a pyrrolehydantoin derivative. Discrepancies between the published spectroscopic data and that reported in the literature cast doubts either on the assigned structure or the reported data.
Bhandari
Manojkumar R
MR
Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas 76019, USA.
Sivappa
Rasapalli
R
Lovely
Carl J
CJ
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
D000470:Alkaloids; D007093:Imidazoles; D011758:Pyrroles; C540090:nagelamide D