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 (Germany)
Volume52
Issue number6
DOIs
Publication statusPublished - 2020 Mar 17

Keywords

  • asymmetric nitroaldol reactions
  • cyclic guanidines
  • enduracididines
  • guanidine functionalization
  • nonproteinogenic amino acids

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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