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

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

Research output: Contribution to journal › Article

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

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RNA-Directed DNA Polymerase
Cycloaddition Reaction
Viruses
Human immunodeficiency virus 1 reverse transcriptase
drimane

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Total synthesis of (-)-mniopetal F, a novel inhibitor of RNA-directed DNA-polymerases. / Suzuki, Yoshikazu; Ohara, Aiko; Sugaya, Kenji; Takao, Kenichi; Tadano, Kin Ichi.

In: Tetrahedron, Vol. 57, No. 34, 20.08.2001, p. 7291-7301.

Research output: Contribution to journal › Article

Suzuki, Y, Ohara, A, Sugaya, K, Takao, K & Tadano, KI 2001, 'Total synthesis of (-)-mniopetal F, a novel inhibitor of RNA-directed DNA-polymerases', Tetrahedron, vol. 57, no. 34, pp. 7291-7301. https://doi.org/10.1016/S0040-4020(01)00686-X
Suzuki Y, Ohara A, Sugaya K, Takao K, Tadano KI. Total synthesis of (-)-mniopetal F, a novel inhibitor of RNA-directed DNA-polymerases. Tetrahedron. 2001 Aug 20;57(34):7291-7301. https://doi.org/10.1016/S0040-4020(01)00686-X
Suzuki, Yoshikazu ; Ohara, Aiko ; Sugaya, Kenji ; Takao, Kenichi ; Tadano, Kin Ichi. / Total synthesis of (-)-mniopetal F, a novel inhibitor of RNA-directed DNA-polymerases. In: Tetrahedron. 2001 ; Vol. 57, No. 34. pp. 7291-7301.
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