Asymmetric syntheses of diarylheptanoid natural products (-)-centrolobine and (-)-de-O-methylcentrolobine via hetero-Diels-Alder reaction catalyzed by dirhodium(II) tetrakis[(R)-3-(benzene-fused-phthalimido)-2-piperidinonate]

Takuya Washio, Reika Yamaguchi, Takumi Abe, Hisanori Nambu, Masahiro Anada, Shunichi Hashimoto

Research output: Contribution to journalArticlepeer-review

49 Citations (Scopus)

Abstract

Catalytic asymmetric syntheses of (-)-centrolobine and (-)-de-O-methylcentrolobine have been achieved, incorporating a hetero-Diels-Alder (HDA) reaction between 4-aryl-2-silyloxy-1,3-butadienes and phenylpropargyl aldehyde derivatives as a key step. The HDA reaction using dirhodium(II) tetrakis[(R)-3-(benzene-fused-phthalimido)-2-piperidinonate], Rh2(R-BPTPI)4, as a chiral Lewis acid catalyst provides exclusively cis-2,6-disubstituted tetrahydropyran-4-ones in up to 93% ee.

Original languageEnglish
Pages (from-to)12037-12046
Number of pages10
JournalTetrahedron
Volume63
Issue number48
DOIs
Publication statusPublished - Nov 26 2007
Externally publishedYes

Keywords

  • (-)-Centrolobine
  • (-)-De-O-methylcentrolobine
  • Chiral Rh(II) catalyst
  • Diarylheptanoids
  • Hetero-Diels-Alder reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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