title: Stereocontrolled and efficient total synthesis of (-)-stephanotic acid methyl ester and (-)-celogentin C.
abstract: 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.
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing 100191, China.
authors.forename: Weimin
authors.initials: W
authors.lastname: Hu
authors.forename: Fengying
authors.initials: F
authors.lastname: Zhang
authors.forename: Zhengren
authors.initials: Z
authors.lastname: Xu
authors.forename: Qiang
authors.initials: Q
authors.lastname: Liu
authors.forename: Yuxin
authors.initials: Y
authors.lastname: Cui
authors.forename: Yanxing
authors.initials: Y
authors.lastname: Jia
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000970:Antineoplastic Agents; D010456:Peptides, Cyclic; C445725:celogentin C; C517105:stephanotic acid methyl ester