Synthetic Studies on the Starfish Alkaloid Imbricatine. Construction of an ent-Imbricatine Framework.

• OHBA Masashi

• IMASHO Masaaki

• FUJII Tozo

Abstract

A chiral synthetic route to the amino esters 5 and 6, which contain the fundamental framework of ent-imbricatine (ent-3), has been developed as a prelude to the total synthesis of the starfish alkaloid imbricatine (3). The route started from the sulfur-containing L-phenylalanine derivative 7 and proceeded through key steps such as cyclization fo the amide 8 without racemization, reduction to the 1, 3-cis-tetrahydroisoquinoline 9, and introduction of a chiral α-amino acid moiety into the chloride 18 by the "bis-lactim ether" method.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 47 (1), 83-89, 1999

  The Pharmaceutical Society of Japan

Keywords

• imbricatine
• benzyltetrahydroisoquinoline alkaloid
• arylthiohistidine synthesis
• Bischler-Napieralski cyclization
• X-ray analysis
• bis-lactim ether

Details

• CRID: 1390001204163657984
• NII Article ID: 130003947674
• NII Article ID: 110003617080
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.47.83
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 3087302
• Web Site: http://hdl.handle.net/2297/7600
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I3087302
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/47/1/47_1_83/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • IRDB
  • NDL
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed