The total synthesis and structure-activity relationships of a highly cytotoxic depsipeptide kulokekahilide-2 and its analogs

被引：13

作者：

Takada, Yuuki ^{[1
]}

Umehara, Masahiro ^{[1
]}

Katsumata, Ryosuke ^{[2
]}

Nakao, Yoichi ^{[2
]}

Kimura, Junji ^{[1
]}

机构：

[1] Aoyama Gakuin Univ, Coll Sci & Engn, Dept Chem & Biol Sci, Chuo Ku, Sagamihara, Kanagawa 2525258, Japan

[2] Waseda Univ, Sch Adv Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, Tokyo 1698555, Japan

来源：

TETRAHEDRON | 2012年 / 68卷 / 02期

基金：

日本学术振兴会;

关键词：

Kulokekahilide-2; Cyclic depsipeptide; Cytotoxicity; Total synthesis; Structure-activity relationships; MARINE CYANOBACTERIUM LYNGBYA; HARE DOLABELLA-AURICULARIA; CANCER CELL-LINES; PEPTIDE ANTIBIOTICS; AURILIDE ANALOGS; MIXED ANHYDRIDE; AMINO-ACIDS; DERIVATIVES; PALAUAMIDE; 1-HYDROXY-7-AZABENZOTRIAZOLE;

D O I：

10.1016/j.tet.2011.10.094

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We successfully completed the total synthesis of kulokekahilide-2, a cytotoxic depsipeptide from the Cephalaspiedean mollusk Phillinopsis speciosa. We have revised the absolute stereochemistry of kulokekahilide-2 to 21-L-Ala, 24-D-MePhe, 37-L-Ile, 43-D-Ala, 15-D-Hica, and 5S,6S,7S-Dtda. We also investigated the cause of the mis-assignment of the configuration in the originally proposed kulokekahilide-2 and concluded that methanolysis using MeONa caused partial racemization, which led to the mis-assignment. The structure activity relationships of kulokekahilide-2 and its analogs indicate the importance of an L-amino acid at position 21. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：659 / 669

页数：11

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