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.
Powell
David A
DA
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.
Batey
Robert A
RA
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