Asymmetric Total Synthesis of Andranginine and Absolute Configuration of Natural Product Isolated from Kopsia arborea

• Kogure Noriyuki

  Graduate School of Pharmaceutical Sciences, Chiba University

Bibliographic Information

Other Title

• アンドランギニンの不斉全合成と天然物の絶対立体配置について
• アンド ランギニン ノ フセイ ゼン ゴウセイ ト テンネンブツ ノ ゼッタイ リッタイ ハイチ ニ ツイテ

Abstract

Andranginine, a pentacyclic monoterpenoid indole alkaloid having hexahydroquinoline-ring and azepine fused structure, was first isolated as a racemate from Craspidospermum verticillatum in 1974. On the other hand, our andranginine isolated from Kopsia arborea exhibited optical activity. In order to find out the mystery on absolute configuration of andranginine, we carried out the asymmetric total synthesis. The first asymmetric total synthesis of andranginine utilizing asymmetric Morita-Baylis-Hillman reaction and diastereoselective intramolecular Diels-Alder reaction has revealed that natural andranginine isolated from K. arborea existed as a scalemic mixture.

Journal

• Journal of Synthetic Organic Chemistry, Japan

  Journal of Synthetic Organic Chemistry, Japan 76 (5), 446-449, 2018-05-01

  The Society of Synthetic Organic Chemistry, Japan

Keywords

• andranginine
• asymmetric total synthesis
• intramolecular Diels-Alder reaction (IMDA)
• Morita-Baylis-Hillman reaction
• scalemic mixture
• biosynthesis
• racemization

Details

• CRID: 1390001205339489664
• NII Article ID: 130006733941
• NII Book ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.76.446
• ISSN: 18836526
• ISSN: 00379980
• NDL BIB ID: 029057606
• Web Site: http://id.ndl.go.jp/bib/029057606
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I029057606
• Web Site: https://www.jstage.jst.go.jp/article/yukigoseikyokaishi/76/5/76_446/_pdf
• Text Lang: ja
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed