Stereoselective synthesis of protected l-allo-Enduracididine and l-Enduracididine via asymmetric nitroaldol reaction

Kosuke Ohsawa, Hongbin Zhao, Takuya Tokunaga, Carys Thomas, A. Ganesan, Yuichi Masuda, Takayuki Doi

Research output: Contribution to journalArticlepeer-review

Abstract

The diastereoselecetive and scalable synthesis of cyclic guanidine-containing nonproteinoginic amino acids, enduracididines, has been achieved. Both diastereomers, l-allo-enduracididine and l-enduracididine, were prepared via catalyst-controlled asymmetric nitroaldol reaction with the aldehyde precursor derived from l-aspartic acid. The cyclic guanidine of di-Cbz-protected l-allo-enduracididine was fully protected with an allyl group to suppress nucleophilic side reactions. Introduced allyl group was efficiently removed via π-allylpalladium chemistry without attaching the Cbz group on the cyclic guanidine moiety.
Original languageEnglish
Pages (from-to)942-948
Number of pages7
JournalSynthesis
Volume52
Issue number6
Early online date26 Nov 2019
DOIs
Publication statusPublished - 17 Mar 2020

Keywords

  • AMINO-ACID
  • ANTIBACTERIAL
  • COMPONENT
  • PEPTIDE
  • SUBSTITUTION
  • TEIXOBACTIN ANALOGS
  • asymmetric nitroaldol reactions
  • cyclic guanidines
  • enduracididines
  • guanidine functionalization
  • nonproteinogenic amino acids

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