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

doi:10.1016/S0040-4020(01)00686-X

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

Department of Applied Chemistry

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 language	English
Pages (from-to)	7291-7301
Number of pages	11
Journal	Tetrahedron
Volume	57
Issue number	34
DOIs	https://doi.org/10.1016/S0040-4020(01)00686-X
Publication status	Published - 2001 Aug 20

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Keywords

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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Suzuki, Y., Ohara, A., Sugaya, K., Takao, K. I., & Tadano, K. I. (2001). Total synthesis of (-)-mniopetal F, a novel inhibitor of RNA-directed DNA-polymerases. Tetrahedron, 57(34), 7291-7301. https://doi.org/10.1016/S0040-4020(01)00686-X

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AU - Tadano, Kin Ichi

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10.1016/S0040-4020(01)00686-X