Stereocontrolled and efficient total synthesis of (-)-stephanotic acid methyl ester and (-)-celogentin C.
A highly stereocontrolled and efficient total synthesis of (-)-stephanotic acid methyl ester and (-)-celogentin C was accomplished in longest linear 14 steps (4.6% overall yield) and in 20 steps (1.6% overall yield) from l-tryptophan, respectively. Highlights of the synthesis include a tandem asymmetric Michael addition/bromination/azidation strategy for a ready access to the leucine-tryptophan moiety (Leu-Trp linkage) and an oxidative coupling reaction to form the indole-imidazole linkage.
Hu
Weimin
W
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing 100191, China.
Zhang
Fengying
F
Xu
Zhengren
Z
Liu
Qiang
Q
Cui
Yuxin
Y
Jia
Yanxing
Y
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000970:Antineoplastic Agents; D010456:Peptides, Cyclic; C445725:celogentin C; C517105:stephanotic acid methyl ester