Asymmetric synthesis of (-)-lentiginosine by double aza-michael reaction

Sin Wei Liu, He Chu Hsu, Chiao Hsin Changa, Hui Hsu Gavin Tsai, Duen Ren Hou

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

Total synthesis of (-)-lentiginosine (1) was achieved in nine steps from (3R,4R)-3,4-dihydroxy-l,5-hexadiene (2). Cross metathesis, vinyl addition and DDQ oxidation were applied to generate the key 3-oxonona-1,4,8-triene 6, which was cyclised to 4-oxopiperidine 7 by diastereoselective double aza-Michael reaction. Both theoretical and empirical studies support that the stereochemical assignment of the major Michael adduct is the desired (2R)-4-oxopiperidme 7.

Original languageEnglish
Pages (from-to)4771-4773
Number of pages3
JournalEuropean Journal of Organic Chemistry
Issue number25
DOIs
StatePublished - Sep 2010

Keywords

  • Alkaloids
  • Asymmetric synthesis
  • Aza-Michael reaction
  • Metathesis

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