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A Flexible Asymmetric Approach to Methyl 5-Alkyltetramates and Its Application in the Synthesis of Cytotoxic Marine Natural Product Belamide A

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A Flexible Asymmetric Approach to Methyl 5-Alkyltetramates and Its Application in the Synthesis of Cytotoxic Marine Natural Product Belamide A.htm (409bytes)
Date
2011-11-19
Author
Lan, Hong-Qiao
Ye, Jian-Liang
Wang, Ai-E
王爱娥
Ruan, Yuan-Ping
阮源萍
Huang, Pei-Qiang
黄培强
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  • 化学化工-已发表论文 [14469]
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Abstract
By using a methyl tetramate derivative (R)- or (S)-9 as a novel chiral building block, a direct, flexible, and highly enantioselective approach to methyl (R)- or (S)-5-alkyltetramates (2) is disclosed. Among the synthesized methyl 5-alkyltetramates 2, methyl 5-methyltetramate (2a) is found in cytotoxic mirabimide E (4) and dysideapyrrolidone (5), and methyl 5-benzyltetramate (2g) is a substructure in the potent antineoplastic dolastatin 15 (3). On the basis of this method, the first asymmetric synthesis of the antimitotic tetrapeptide belamide A (7) has been achieved in seven steps from (S)-9, with an overall yield of 23.8%. Not only have the structure and absolute configuration of (+)-belamide A (7) been confirmed, but also the solvent used for recording the (13)C NMR spectrum, the (13)C NMR spectrum data correlation, and optical rotation data of natural belamide A (7) have been revised.
Citation
CHEMISTRY-A EUROPEAN JOURNAL,2011,17(3):958-968
URI
http://dx.doi.org/doi:10.1002/chem.201002063
WOS:000287259700030
https://dspace.xmu.edu.cn/handle/2288/11985

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