Total synthesis of the opioid agonistic indole alkaloid mitragynine and the first total syntheses of 9-methoxygeissoschizol and 9-methoxy-Nb-methylgeissoschizol.
An enantiospecific method for the synthesis of 4-methoxytryptophan has been developed via a regiospecific Larock heteroannulation and employed for the first total syntheses of 9-methoxygeissoschizol and 9-methoxy-Nb-methylgeissoschizol, as well as the total synthesis of the opioid agonistic alkaloid mitragynine. The asymmetric Pictet-Spengler reaction and a Ni(COD)2-mediated cyclization served as key steps.
Ma
Jun
J
Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, 3210 N. Cramer Street, Milwaukee, Wisconsin 53211, USA.
Yin
Wenyuan
W
Zhou
Hao
H
Cook
James M
JM
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D017450:Receptors, Opioid, mu / Q000819:agonists / Q000737:chemistry*; D046948:Secologanin Tryptamine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry
C412061:9-methoxy-Nb-methylgeissoschizol; C524008:9-methoxygeissoschizol; D000470:Alkaloids; D026121:Indole Alkaloids; D007211:Indoles; D017450:Receptors, Opioid, mu; D046948:Secologanin Tryptamine Alkaloids; C001801:mitragynine