Syntheses of a pyrrolidine analog of a tetrahydrofuran containing acetogenin, cis-solamin

Kouji Ohnishi, Haruka Sakurai, Kazuya Kobayashi, Hidefumi Makabe, Kenta Teruya, Kenichi Akaji, Yasunao Hattori

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Practical synthesis of a pyrrolidine analog of a mono-THF acetogenin as a proto-type analog to evaluate the effect of a heteroatom in the mono-THF ring of acetogenins was achieved using Pd(II)-catalyzed diastereo-selective cyclization. Ligand-less PdCl 2 catalyzed cyclization yielded the desired pyrrolidine derivative as a single major product having the desired relative configurations. Coupling of the pyrrolidine fragment with a known γ-lactone-containing fragment via a Sonogashira cross-coupling reaction yielded the desired aza-cis-solamin analog.

Original languageEnglish
Pages (from-to)573-582
Number of pages10
JournalHeterocycles
Volume91
Issue number3
DOIs
Publication statusPublished - 2015

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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