Total synthesis of (-)-agelastatin A

Takehiko Yoshimitsu, Tatsunori Ino, Tetsuaki Tanaka

Research output: Contribution to journalArticle

56 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 - 2008
Externally publishedYes

Fingerprint

Cyclization
ureas
hydrolysis
routes
Oxazolidinones
nitrogen
preparation
synthesis
Urea
Hydrolysis
Nitrogen
agelastatin A

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Total synthesis of (-)-agelastatin A. / Yoshimitsu, Takehiko; Ino, Tatsunori; Tanaka, Tetsuaki.

In: Organic Letters, Vol. 10, No. 23, 2008, p. 5457-5460.

Research output: Contribution to journalArticle

Yoshimitsu, T, Ino, T & Tanaka, T 2008, 'Total synthesis of (-)-agelastatin A', Organic Letters, vol. 10, no. 23, pp. 5457-5460. https://doi.org/10.1021/ol802225g
Yoshimitsu, Takehiko ; Ino, Tatsunori ; Tanaka, Tetsuaki. / Total synthesis of (-)-agelastatin A. In: Organic Letters. 2008 ; Vol. 10, No. 23. pp. 5457-5460.
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