An approach for the synthesis of nakamuric acid

Xiaolei Wang, Chuo Chen

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The biosynthesis of dimeric pyrrole-imidazole alkaloids is likely mediated by enzyme-catalyzed reversible single-electron transfer (SET) cycloaddition. We now show that Ir(ppy)<inf>3</inf> can promote SET-mediated formal [2+2] and [4+2] cycloaddition reactions of pyrrole-imidazole alkaloids-related substrates under photolytic conditions. This biomimetic approach is useful for the construction of the core skeleton of nakamuric acid and sceptrin.

Original languageEnglish (US)
Pages (from-to)3690-3693
Number of pages4
JournalTetrahedron
Volume71
Issue number22
DOIs
StatePublished - Jun 3 2015

Fingerprint

Pyrroles
Cycloaddition
Cycloaddition Reaction
Alkaloids
Electrons
Biomimetics
Biosynthesis
Skeleton
Substrates
Enzymes
imidazole
nakamuric acid
sceptrin

Keywords

  • Cyclization
  • Imidazole
  • Pyrrole
  • Radical
  • Single-electron transfer

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

An approach for the synthesis of nakamuric acid. / Wang, Xiaolei; Chen, Chuo.

In: Tetrahedron, Vol. 71, No. 22, 03.06.2015, p. 3690-3693.

Research output: Contribution to journalArticle

Wang, Xiaolei ; Chen, Chuo. / An approach for the synthesis of nakamuric acid. In: Tetrahedron. 2015 ; Vol. 71, No. 22. pp. 3690-3693.
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