Divergent synthesis of 2,6-disubstituted piperidine alkaloid, (+)-spectaline by palladium-catalyzed cyclization

Masatomo Katsuyama, Masahiro Furuta, Kazuya Kobayashi, Kenta Teruya, Hidefumi Makabe, Kenichi Akaji, Yasunao Hattori

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Convergent synthesis of 2,6-disubstituted piperidine alkaloid, (+)-spectaline is described. Using substrate-controlled diastereo-selective Pd(II)-catalyzed cyclization, both cis-2,6- and trans-2,6-disubstituted piperidine backbones were constructed from adequately protected precursors with high selectivity. Synthesis of (+)-spectaline containing cis-2,6-disubstituents was accomplished by 10 step reactions with a 31% total yield.

Original languageEnglish
Pages (from-to)959-969
Number of pages11
JournalHeterocycles
Volume91
Issue number5
DOIs
Publication statusPublished - 2015
Externally publishedYes

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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