First total synthesis of martinellic acid, a naturally occurring bradykinin receptor antagonist.
[reaction: see text] The first total synthesis of martinellic acid, a naturally occurring bradykinin receptor antagonist, via a CuI-catalyzed coupling reaction of beta-amino ester 6 with 1,4-diiodobenzene and a guanylation reaction of secondary amine 3 under mild conditions as key steps, is described.
Ma
D
D
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, 354 Fenglin Lu, Shanghai 200032, China. madw@pub.sioc.ac.cn
Xia
C
C
Jiang
J
J
Zhang
J
J
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry; D065168:Bradykinin Receptor Antagonists; D015394:Molecular Structure; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018002:Receptors, Bradykinin / Q000378:metabolism; D013329:Structure-Activity Relationship
D000470:Alkaloids; D000588:Amines; D065168:Bradykinin Receptor Antagonists; D011758:Pyrroles; D011804:Quinolines; D018002:Receptors, Bradykinin; C432345:martinellic acid; C410408:martinelline