Total synthesis of maremycins A,B, C1/C2, D1, and D2 |
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Authors: | Yonghua Liu Liangren Zhang Yanxing Jia |
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Institution: | 1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing 100191, China;2. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China |
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Abstract: | The total synthesis of maremycins A, B, C1/C2, D1, and D2 is achieved starting from the natural amino acids l-isoleucine and S-methyl-l-cysteine, in which the total synthesis of maremycins B, C1/C2, and D2 is accomplished for the first time. The synthesis features a position-selective intramolecular bromination process for the synthesis of key chiral building block, a Pd-catalyzed indole synthesis for the preparation of (2S,3S)-β-methyltryptophan and hydroxylation of oxindoles by molecular oxygen. In addition, the protocol for conversion of maremycins A and B to maremycins C and D was improved. |
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