Total synthesis of the β-caten in inhibitor, (-)-agelastatin A: A second-generation approach based on radical aminobromination

Takehiko Yoshimitsu, Tatsunori Ino, Naoyuki Futamura, Takuma Kamon, Tetsuaki Tanaka

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

The second-generation approach to (-)-agelastatin A has been established. The present strategy features the FeBr2-mediated radical cyclization of 2-cyclopentenyloxycarbonyl azide that allows for the stereoselective installation of a cis-vicinal aminobromo functionality suitable for producing the BCD-ring system of agelastatin A. The aminobromination method streamlines access to oxazolidinone, a key intermediate in the previously reported synthesis, thereby culminating in the new total synthesis of (-)-agelastatin A.

Original languageEnglish
Pages (from-to)3402-3405
Number of pages4
JournalOrganic Letters
Volume11
Issue number15
DOIs
Publication statusPublished - Aug 6 2009
Externally publishedYes

Fingerprint

inhibitors
synthesis
Oxazolidinones
installing
Azides
Cyclization
rings
agelastatin A

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Total synthesis of the β-caten in inhibitor, (-)-agelastatin A : A second-generation approach based on radical aminobromination. / Yoshimitsu, Takehiko; Ino, Tatsunori; Futamura, Naoyuki; Kamon, Takuma; Tanaka, Tetsuaki.

In: Organic Letters, Vol. 11, No. 15, 06.08.2009, p. 3402-3405.

Research output: Contribution to journalArticle

Yoshimitsu, Takehiko ; Ino, Tatsunori ; Futamura, Naoyuki ; Kamon, Takuma ; Tanaka, Tetsuaki. / Total synthesis of the β-caten in inhibitor, (-)-agelastatin A : A second-generation approach based on radical aminobromination. In: Organic Letters. 2009 ; Vol. 11, No. 15. pp. 3402-3405.
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