Unified Total Synthesis of Five Gelsedine-Type Alkaloids: (−)-Gelsenicine, (−)-Gelsedine, (−)-Gelsedilam, (−)-14-Hydroxygelsenicine, and (−)-14,15-Dihydroxygelsenicine

• Harada, Takaaki

• Shimokawa, Jun

• Fukuyama, Tohru

Abstract

The systematic arrangement of a two-carbon unit, hydrogen atom, and oxygen atom on the versatile enal moiety of a non-natural synthetic intermediate successfully led to the unified access to the gelsedine-type alkaloids. The development and use of this new synthetic hub and an array of site-selective transformations resulted in the asymmetric synthesis of (−)-gelsenicine, (−)-gelsedine, (−)-gelsedilam, (−)-14-hydroxygelsenicine, and (−)-14,15-dihydroxygelsenicine.

Journal

• Organic Letters

  Organic Letters 18 (18), 4622-4625, 2016-08-31

  ACS Publications

Keywords

• Organic Chemistry
• Physical and Theoretical Chemistry
• Biochemistry

Details

• CRID: 1050001338805672320
• NII Article ID: 120005946825
• DOI: 10.1021/acs.orglett.6b02263
• ISSN: 15237052
• ISSN: 15237060
• HANDLE: 2237/25410
• Web Site: https://nagoya.repo.nii.ac.jp/records/23216
• Web Site: https://pubs.acs.org/doi/pdf/10.1021/acs.orglett.6b02263
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • Crossref
  • CiNii Articles
  • KAKEN