Concise syntheses of dictyodendrins A and F by a sequential C-H functionalization strategy

Atsushi D. Yamaguchi, Kathryn M. Chepiga, Junichiro Yamaguchi, Kenichiro Itami, Huw M L Davies

Research output: Contribution to journalArticle

68 Citations (Scopus)

Abstract

Syntheses of dictyodendrins A and F have been achieved using a sequential C-H functionalization strategy. The N-alkylpyrrole core is fully functionalized by means of a rhodium(I)-catalyzed C-H arylation at the C3-position, a rhodium(II)-catalyzed double C-H insertion at the C2- and C5-positions, and a Suzuki-Miyaura cross-coupling reaction at the C4-position. The syntheses of dictyodendrins A and F were completed by formal 6π-electrocyclization to generate the pyrrolo[2,3-c]carbazole core of the natural products.

Original languageEnglish
Pages (from-to)644-647
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number2
DOIs
Publication statusPublished - 2015 Jan 21
Externally publishedYes

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Rhodium
Cross Reactions
Biological Products
dictyodendrin A
dictyodendrins F
carbazole

ASJC Scopus subject areas

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

Cite this

Concise syntheses of dictyodendrins A and F by a sequential C-H functionalization strategy. / Yamaguchi, Atsushi D.; Chepiga, Kathryn M.; Yamaguchi, Junichiro; Itami, Kenichiro; Davies, Huw M L.

In: Journal of the American Chemical Society, Vol. 137, No. 2, 21.01.2015, p. 644-647.

Research output: Contribution to journalArticle

Yamaguchi, Atsushi D. ; Chepiga, Kathryn M. ; Yamaguchi, Junichiro ; Itami, Kenichiro ; Davies, Huw M L. / Concise syntheses of dictyodendrins A and F by a sequential C-H functionalization strategy. In: Journal of the American Chemical Society. 2015 ; Vol. 137, No. 2. pp. 644-647.
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