Total synthesis of (-)-agelastatin A

Takehiko Yoshimitsu, Tatsunori Ino, Tetsuaki Tanaka

Research output: Contribution to journalArticlepeer-review

57 Citations (Scopus)

Abstract

(Chemical Equation Presented) A new route to (-)-agelastatin A is reported. The requisite nitrogen functionalities of the agelastatin core have been installed by intramolecular aziridination of an azidoformate and subsequent regioselective azidation, leading to net trans-diamination of the double bond. The present synthesis also demonstrates two new protocols for the preparation of an imidazolidinone hemiaminal motif from an oxazolidinone intermediate which comprise sequential N-tert-butoxycarbonylation, urea formation, hydrolysis, and oxidative cyclization, and direct aminolysis and subsequent oxidative cyclization.

Original languageEnglish
Pages (from-to)5457-5460
Number of pages4
JournalOrganic Letters
Volume10
Issue number23
DOIs
Publication statusPublished - Dec 1 2008
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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