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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

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

Hugh Nakamura, Chihiro Tsukano, Takuma Yoshida, Motohiro Yasui, Shinsuke Yokouchi, Yusuke Kobayashi, Masayuki Igarashi, Yoshiji Takemoto

J Am Chem Soc. 2019 May 29;141(21):8527-8540.

PMID: 31067040

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP7440053-A	Palladium black		7440-05-3	Price

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