Total Synthesis of (±)-Carquinostatin A, and Asymmetric Total Synthesis of (<i>R</i>)-(−)-Carquinostatin A and (<i>S</i>)-(+)-Carquinostatin A

• Hieda Yuhzo

  Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University

• Choshi Tominari

  Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University

• Uchida Yoshinari

  Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University

• Fujioka Haruto

  Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University

• Fujii Sayuri

  Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University

• Hibino Satoshi

  Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University

Bibliographic Information

Other Title

• Total Synthesis of (±)-Carquinostatin A, and Asymmetric Total Synthesis of (R)-(-)-Carquinostatin A and (S)-(+)-Carquinostatin A
• Total Synthesis of (&plusmn;)-Carquinostatin A, and Asymmetric Total Synthesis of (<i>R</i>)-(−)-Carquinostatin A and (<i>S</i>)-(+)-Carquinostatin A

Abstract

Total syntheses of (±)-carquinostatin A (1), and (R)-(−)-carquinostatin A (1a) together with its enantiomer, (S)-(+)-carquinostatin A (1b), possessing radical scavenging activity, were newly achieved. (±)-Carquinostatin A (1) was synthesized from 1-acetonyl-6-bromo-3-ethoxy-2-methylcarbazole (6), which was derived from the known 1-acetonyl-3-ethoxy-2-methylcarbazole (5). Introduction of a prenyl group at the 6-position of carbazole was successful in two steps. For the synthesis of (R)-(−)-carquinostatin A (1a) and (S)-(+)-carquinostatin A (1b), (R)-(−)-1-(2-acetoxypropyl)-3-hydroxy-2-methylcarbazole (15a) and (S)-(+)-3-hydroxy-1-(2-hydroxypropyl)-2-methylcarbazole (15b), prepared by lipase-QLM catalyzed enantioselective transesterification of 3-hydroxy-1-(2-hydroxypropyl)-2-methylcarbazole (14), were used as the chiral starting material.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 60 (12), 1522-1530, 2012

  The Pharmaceutical Society of Japan

Keywords

• total synthesis
• (±)-carquinostatin A
• (<i>R</i>)-(−)-carquinostatin A
• (<i>S</i>)-(+)-carquinostatin A
• lipase-QLM
• asymmetric synthesis

Details

• CRID: 1390001204178060160
• NII Article ID: 130002459933
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.c12-00650
• COI: 1:STN:280:DC%2BC3s7oslKgtw%3D%3D
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 024105085
• PubMed: 23207633
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I024105085
• Web Site: https://www.jstage.jst.go.jp/article/cpb/60/12/60_c12-00650/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed