Total synthesis of (-)-ardeemin.
Total synthesis of potent anti-MDR indole alkaloids (-)-ardeemin and its N-acyl analogues has been accomplished from L-tryptophan with about 2% overall yield in 20 steps. The key step depended on the newly developed three-step one-pot cascade reaction of 7 with diazoester 8 via intermolecular cyclopropanation, ring opening, and ring closure to assemble the chiral 3-substituted hexahydropyrrolo[2,3-b]indole 4a.
He
Bin
B
Department of Chemistry of Medicinal Natural Products, Key Laboratory of Drug Targeting and Novel Delivery System of Ministry of Education, West China School of Pharmacy, Chengdu 610041, PR China.
Song
Hao
H
Du
Yu
Y
Qin
Yong
Y
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D000470:Alkaloids; D026121:Indole Alkaloids; D007211:Indoles; C534892:ardeemin