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 › peer-review

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

Keywords

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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/S0040-4020(01)00686-X

Cite this

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

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.",

keywords = "Biologically active compounds, Diels-Alder reactions, Katsuki-Sharpless reactions, Terpenes and terpenoids",

author = "Yoshikazu Suzuki and Aiko Ohara and Kenji Sugaya and Takao, {Ken Ichi} and Tadano, {Kin Ichi}",

note = "Funding Information: We thank Professor W. Steglich (University of M{\"u}nchen) for sending us copies of the spectra for natural mniopetal F ( 1 H and 13 C NMR and MS). We are grateful to the Japan Interaction in Science and Technology Forum (JIST) for financial support. ",

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doi = "10.1016/S0040-4020(01)00686-X",

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T1 - Total synthesis of (-)-mniopetal F, a novel inhibitor of RNA-directed DNA-polymerases

AU - Suzuki, Yoshikazu

AU - Ohara, Aiko

AU - Sugaya, Kenji

AU - Takao, Ken Ichi

AU - Tadano, Kin Ichi

N1 - Funding Information: We thank Professor W. Steglich (University of München) for sending us copies of the spectra for natural mniopetal F ( 1 H and 13 C NMR and MS). We are grateful to the Japan Interaction in Science and Technology Forum (JIST) for financial support.

PY - 2001/8/20

Y1 - 2001/8/20

N2 - 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.

AB - 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.

KW - Biologically active compounds

KW - Diels-Alder reactions

KW - Katsuki-Sharpless reactions

KW - Terpenes and terpenoids

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DO - 10.1016/S0040-4020(01)00686-X

M3 - Article

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JO - Tetrahedron

JF - Tetrahedron

IS - 34

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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