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

Fingerprint

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.
@article{acc9952b6fd24457aeda6c3673b5acc9,
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 Kenichi Takao and Tadano, {Kin Ichi}",
year = "2001",
month = "8",
day = "20",
doi = "10.1016/S0040-4020(01)00686-X",
language = "English",
volume = "57",
pages = "7291--7301",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "34",

}

TY - JOUR

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, Kenichi

AU - Tadano, Kin Ichi

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

UR - http://www.scopus.com/inward/record.url?scp=0035921061&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035921061&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(01)00686-X

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

M3 - Article

VL - 57

SP - 7291

EP - 7301

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 34

ER -

Access to Document