期刊
TETRAHEDRON
卷 68, 期 2, 页码 659-669出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.10.094
关键词
Kulokekahilide-2; Cyclic depsipeptide; Cytotoxicity; Total synthesis; Structure-activity relationships
资金
- Japan Society for the Promotion of Science [S0901031, 1931013B]
- Ministry of Education, Culture, Sports, Science and Technology (MEXT)
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.
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