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Title: 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
Authors: Nakamura, Hugh
Tsukano, Chihiro
Yoshida, Takuma
Yasui, Motohiro
Yokouchi, Shinsuke
Kobayashi, Yusuke
Igarashi, Masayuki
Takemoto, Yoshiji
Author's alias: 塚野, 千尋
小林, 祐輔
竹本, 佳司
Issue Date: 29-May-2019
Publisher: American Chemical Society (ACS)
Journal title: Journal of the American Chemical Society
Volume: 141
Issue: 21
Start page: 8527
End page: 8540
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.
Rights: This is the accepted manuscript of the article, which has been published in final form at https://doi.org/10.1021/jacs.9b02220.
The full-text file will be made open to the public on 8 May 2020 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.
This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
URI: http://hdl.handle.net/2433/243177
DOI(Published Version): 10.1021/jacs.9b02220
PubMed ID: 31067040
Appears in Collections:Journal Articles

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