First Total Synthesis of the Pavine Alkaloid (±)-Neocaryachine and Its Optical Resolution

• Miura Yuta

  School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University

• Saito Yohei

  School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University

• Goto Masuo

  Division of Chemical Biology and Medicinal Chemistry, UNC Eshelman School of Pharmacy, University of North Carolina

• Nakagawa-Goto Kyoko

  School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University Division of Chemical Biology and Medicinal Chemistry, UNC Eshelman School of Pharmacy, University of North Carolina

Abstract

The first total synthesis of (±)-neocaryachine (1) was achieved using a radical cyclization to produce the dibenzo-9-azabicyclo[3.3.1]nonane pavine skeleton, following a Bischler–Napieralski reaction to construct an intermediate benzylisoquinoline. The resulting racemic mixture was separated by chiral column chromatography to provide pure (+)- and (−)-1.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 68 (9), 899-902, 2020-09-01

  The Pharmaceutical Society of Japan

Keywords

• pavine alkaloid
• neocaryachine
• total synthesis
• optical resolution

Details

• CRID: 1390003825209734016
• NII Article ID: 130007893858
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.c20-00370
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 030606026
• PubMed: 32879231
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I030606026
• Web Site: https://www.jstage.jst.go.jp/article/cpb/68/9/68_c20-00370/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed