Synthetic Study of Matrine-Type Alkaloids: Stereoselective Construction of the AB Rings of the Quinolizidine Skeleton

• Tsukano, Chihiro

• Oimura, Atsuko

• Enkhtaivan, Iderbat

• Takemoto, Yoshiji

Abstract

A new method has been developed for the stereoselective construction of the AB rings of the quinolizidine skeleton of ­matrine-type alkaloids with a cis-cis stereochemistry. The key features of this method involve: (i) construction of the quinolizidine by reduction of an acylpyridinium cation; and (ii) late-stage introduction of methoxypyridine by sequential Stille coupling and diastereo­selective hydrogenation reactions.

Journal

• Synlett

  Synlett 25 (5), 653-656, 2014-03-05

  Thieme Publishing Group

Keywords

• quinolizidines
• stereoselective synthesis
• alkaloids
• matrine
• pyridines

Details

• CRID: 1050564285767057920
• NII Article ID: 120005651944
• NII Book ID: AA10731110
• ISSN: 09365214
• ISSN: 14372096
• DOI: 10.1055/s-0033-1340179
• HANDLE: 2433/199887
• Web Site: http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0033-1340179.pdf
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • Crossref
  • CiNii Articles
  • KAKEN