期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 141, 期 21, 页码 8527-8540出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b02220
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资金
- JSPS KAKENHI [JP17H050.51, JP16H06384]
- JSPS KAKENHI in the Middle Molecular Strategy [JP18H04407]
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-beta-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.
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