Total synthesis of the alkaloids martinelline and martinellic acid via a hetero Diels-Alder multicomponent coupling reaction.
[reaction: see text] A concise synthesis of the guanidine alkaloids, (+/-)-martinelline and (+/-)-martinellic acid, using a protic acid catalyzed 2:1 hetero Diels-Alder coupling reaction between N-Cbz 2-pyrroline and methyl 4-aminobenzoate, is described. Protic acid catalysis, rather than Lewis acid catalysis, was necessary to achieve the desired sense of diastereocontrol in the coupling reaction.
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.
David A
DA
Powell
Robert A
RA
Batey
D010129:4-Aminobenzoic Acid / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D065168:Bradykinin Receptor Antagonists; D019791:Guanidine / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis*; D062366:para-Aminobenzoates
D000470:Alkaloids; D000900:Anti-Bacterial Agents; D065168:Bradykinin Receptor Antagonists; D011758:Pyrroles; D011804:Quinolines; C432345:martinellic acid; C410408:martinelline; D062366:para-Aminobenzoates; C013231:pyrroline; C067182:methyl 4-aminobenzoate; D019791:Guanidine; D010129:4-Aminobenzoic Acid