Synthesis of (.+-.)-8-Deisopropyladunctin B

• Nomura Sayo

  Kyoto Pharmaceutical University

• Arimitsu Kenji

  Kyoto Pharmaceutical University

• Yamaguchi Satoshi

  Kyoto Pharmaceutical University

• Kosuga Yuya

  Kyoto Pharmaceutical University

• Kakimoto Yuko

  Kyoto Pharmaceutical University

• Komai Takanori

  Kyoto Pharmaceutical University

• Hasegawa Kazumasa

  Kyoto Pharmaceutical University

• Nakanishi Akira

  Kyoto Pharmaceutical University

• Miyoshi Tamami

  Kyoto Pharmaceutical University

• Iwasaki Hiroki

  Kyoto Pharmaceutical University

• Ozeki Minoru

  Kyoto Pharmaceutical University

• Kawasaki Ikuo

  Kyoto Pharmaceutical University

• Kurume Ai

  Kyoto Pharmaceutical University

• Ohta Shunsaku

  Kyoto Pharmaceutical University

• Yamashita Masayuki

  Kyoto Pharmaceutical University

Bibliographic Information

Other Title

• Synthesis of (±)-8-Deisopropyladunctin B

Abstract

(±)-8-Deisopropyladunctin B, the deisopropyl form of adunctin B, which was isolated from the leaves of Piper aduncum (Piperaceae) collected in Papua New Guinea, was synthesized in 0.77% overall yield in 17 steps from 5,7-dimethoxycoumarin-3-carboxylate. The key step was our original stereoconvergent skeleton transformation from 1,2,2a,8b-tetrahydro-3H-benzo[b]cyclobuta[d]pyran-3-one to 1,2,4a,9b-tetrahydrodibenzofuran-4-ol with dimethylsulfoxonium methylide.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 60 (1), 94-103, 2012

  The Pharmaceutical Society of Japan

Keywords

• adunctin B
• 8-deisopropyladunctin B
• total synthesis
• ylide
• skeleton transformation

Details

• CRID: 1390282679153822208
• NII Article ID: 130001852353
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.60.94
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 024029773
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I024029773
• Web Site: http://www.jstage.jst.go.jp/article/cpb/60/1/60_1_94/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed