Total synthesis of (-)-mniopetal F, a novel inhibitor of RNA-directed DNA-polymerases

Yoshikazu Suzuki, Aiko Ohara, Kenji Sugaya, Ken Ichi Takao, Kin Ichi Tadano

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

We have achieved a total synthesis of (-)-mniopetal F, a drimane-type sesquiterpenoid which inhibits the reverse transcriptase activity of the human immunodeficiency virus (HIV)-1. The key step in our enantiospecific synthesis is a stereoselective intramolecular Diels-Alder reaction, in which the π-facial selectivity is controlled by the stereoelectronic effect of a trialkylsilyloxy substituent existing adjacent to the dienophile part.

Original languageEnglish
Pages (from-to)7291-7301
Number of pages11
JournalTetrahedron
Volume57
Issue number34
DOIs
Publication statusPublished - 2001 Aug 20

Keywords

  • Biologically active compounds
  • Diels-Alder reactions
  • Katsuki-Sharpless reactions
  • Terpenes and terpenoids

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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