Synthesis of the oxazolidinone fragment of thelepamide

Naoki Ashida, Kousuke Ida, Yumi Koide, Christopher J. Vavricka, Minoru Izumi, Hiromasa Kiyota

Research output: Contribution to journalArticle

Abstract

Thelepamide, an unique ketide-amino acid isolated from a marine annelid worm Thelepus crispus, has a unique oxazolidinone ring derived from cysteine, glycine and valine. Rareness in nature as well as promising bioactive possibility make the oxazolidinone ring an attractive synthetic target. The hydroxy oxazolidinone fragment of thelepamide was prepared by acid-catalysed N,O-acetal formation between a ketoamide and formaldehyde. Lactone-carbonyl selective isopropyl addition to an oxazilidine–dione under Grignard conditions also forms the target compound.

Original languageEnglish
JournalNatural Product Research
DOIs
Publication statusAccepted/In press - 2020

Keywords

  • ethanamic acid
  • N,O-acetal
  • oxazolidinone
  • sealed tube
  • synthesis
  • thelepamide
  • Word

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Plant Science
  • Organic Chemistry

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