Studies on the synthesis of orthogonally protected azalanthionines, and of routes towards β-methyl azalanthionines, by ring opening of N-activated aziridine-2-carboxylates

Keith O'Brien, Keith Ó Proinsias, Fintan Kelleher

Research output: Contribution to journalArticlepeer-review

Abstract

Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para- methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding β-methyl azalanthionines have, so far, been unsuccessful.

Original languageEnglish
Pages (from-to)5082-5092
Number of pages11
JournalTetrahedron
Volume70
Issue number34
DOIs
Publication statusPublished - 26 Aug 2014

Keywords

  • 1,2-Diaminopropanoic acids (DAPs)
  • Azalanthionines
  • Aziridine-2-carboxylates
  • Lanthionine
  • Ring-opening
  • β-Methyl azalanthionines

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