Synthesis of dragmacidin D via direct C-H couplings

Debashis Mandal, Atsushi D. Yamaguchi, Junichiro Yamaguchi, Kenichiro Itami

Research output: Contribution to journalArticle

110 Citations (Scopus)

Abstract

Dragmacidin D, an emerging biologically active marine natural product, has attracted attention as a lead compound for treating Parkinson's and Alzheimer's diseases. Prominent structural features of this compound are the two indole-pyrazinone bonds and the presence of a polar aminoimidazole unit. We have established a concise total synthesis of dragmacidin D using direct C-H coupling reactions. Methodological developments include (i) Pd-catalyzed thiophene-indole C-H/C-I coupling, (ii) Pd-catalyzed indole-pyrazine N-oxide C-H/C-H coupling, and (iii) acid-catalyzed indole-pyrazinone C-H/C-H coupling. These regioselective catalytic C-H couplings enabled us to rapidly assemble simple building blocks to construct the core structure of dragmacidin D in a step-economical fashion.

Original languageEnglish
Pages (from-to)19660-19663
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number49
DOIs
Publication statusPublished - 2011 Dec 14
Externally publishedYes

Fingerprint

Lead compounds
Thiophene
Oxides
Acids
Pyrazines
Thiophenes
Biological Products
Parkinson Disease
Alzheimer Disease
indole
dragmacidin D

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Synthesis of dragmacidin D via direct C-H couplings. / Mandal, Debashis; Yamaguchi, Atsushi D.; Yamaguchi, Junichiro; Itami, Kenichiro.

In: Journal of the American Chemical Society, Vol. 133, No. 49, 14.12.2011, p. 19660-19663.

Research output: Contribution to journalArticle

Mandal, Debashis ; Yamaguchi, Atsushi D. ; Yamaguchi, Junichiro ; Itami, Kenichiro. / Synthesis of dragmacidin D via direct C-H couplings. In: Journal of the American Chemical Society. 2011 ; Vol. 133, No. 49. pp. 19660-19663.
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