Full Paper

Enantioselective Total Synthesis of (+)-Stachyflin: A Potential Anti-Influenza A Virus Agent Isolated from a Microorganism

  1. Junji Sakurai1,
  2. Takuya Kikuchi1,
  3. Ohgi Takahashi2,
  4. Kazuhiro Watanabe1,
  5. Tadashi Katoh1

Article first published online: 18 APR 2011

DOI: 10.1002/ejoc.201100173

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2011, Issue 16, pages 2948–2957, June 2011

Additional Information

How to Cite

Sakurai, J., Kikuchi, T., Takahashi, O., Watanabe, K. and Katoh, T. (2011), Enantioselective Total Synthesis of (+)-Stachyflin: A Potential Anti-Influenza A Virus Agent Isolated from a Microorganism. Eur. J. Org. Chem., 2011: 2948–2957. doi: 10.1002/ejoc.201100173

Author Information

  1. 1

    Laboratory of Synthetic Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan, Fax: +81-22-727-0135

  2. 2

    Laboratory of Pharmaceutical Physical Chemistry, Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan

Publication History

  1. Issue published online: 19 MAY 2011
  2. Article first published online: 18 APR 2011
  3. Manuscript Received: 6 FEB 2011

Funded by

  • Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT). Grant Numbers: 17035073, 17035073, 18032065, 18590013, 21590018

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Keywords:

  • Natural products;
  • Total synthesis;
  • Stachyflin;
  • Influenza A;
  • Antiviral agents;
  • Hemagglutinin inhibitor

Abstract

A novel and potent hemagglutinin inhibitor, (+)-stachyflin, was efficiently synthesized in an enantioselective manner starting from the (+)-5-methyl-Wieland–Miescher ketone. The synthetic method features a BF3·Et2O-induced cascade epoxide-opening/rearrangement/cyclization reaction tostereoselectively construct the requisite pentacyclic ring system in one step. In order to rationalize the mechanism of the cascade reaction, quantum chemical calculations of the possible intermediary carbocations and transition states in the model synthesis were carried out. An alternative approach to synthesize (+)-stachyflin by employing a similar cascade reaction was also described.

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