Total Synthesis of Caprazamycin A: Practical and Scalable Synthesis of syn-β-Hydroxyamino Acids and Introduction of a Fatty Acid Side Chain to 1,4-Diazepanone
| Autor: | Yoshiji Takemoto, Chihiro Tsukano, Takuma Yoshida, Shinsuke Yokouchi, Yusuke Kobayashi, Hugh Nakamura, Masayuki Igarashi, Motohiro Yasui |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Formic acid Fatty Acids Molecular Conformation Fatty acid Total synthesis Stereoisomerism Azepines General Chemistry 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Catalysis Uridine 0104 chemical sciences Palladium black chemistry.chemical_compound Colloid and Surface Chemistry chemistry Aldol reaction Side chain Mitsunobu reaction Amino Acids |
| Zdroj: | Journal of the American Chemical Society. 141:8527-8540 |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/jacs.9b02220 |
| Popis: | The first total synthesis of caprazamycin A (1), a representative liponucleoside antibiotic, is described. Diastereoselective aldol reactions of aldehydes 12 and 25–27, derived from uridine, with diethyl isocyanomalonate 13 and phenylcarbamate 21 were investigated using thiourea catalysts 14 or bases to synthesize syn-β-hydroxyamino acid derivatives. The 1, 4-diazepanone core of 1 was constructed using a Mitsunobu reaction, and the fatty acid side chain was introduced using a stepwise sequence based on model studies. Notably, global deprotection was realized using palladium black and formic acid without hydrogenating the olefin in the uridine unit. |
| Databáze: | OpenAIRE |
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