Total synthesis of (-)-mniopetal E, a novel biologically intriguing drimane sesquiterpenoid

Yoshikazu Suzuki; Ryoko Nishimaki; Makoto Ishikawa; Takeshi Murata; Ken ichi Takao; Kin ichi Tadano

doi:10.1016/S0040-4039(99)01631-7

Total synthesis of (-)-mniopetal E, a novel biologically intriguing drimane sesquiterpenoid

Yoshikazu Suzuki, Ryoko Nishimaki, Makoto Ishikawa, Takeshi Murata, Ken ichi Takao, Kin ichi Tadano

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

Total synthesis of (-)-mniopetal E, the common skeleton of the biologically intriguing mniopetals A-D, was accomplished for the first time. The key step of the total synthesis was stereoselective intramolecular Diels-Alder reaction for construction of the octahydronaphthalene core structure. Our total synthesis as natural enantiomeric form established the unsettled absolute stereochemistry of the antibiotic.

Original language	English
Pages (from-to)	7835-7838
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	44
DOIs	https://doi.org/10.1016/S0040-4039(99)01631-7
Publication status	Published - 1999 Oct 29

Keywords

Biologically active compounds
Diels-Alder reactions
Terpenoids

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Total synthesis of (-)-mniopetal E, a novel biologically intriguing drimane sesquiterpenoid",

abstract = "Total synthesis of (-)-mniopetal E, the common skeleton of the biologically intriguing mniopetals A-D, was accomplished for the first time. The key step of the total synthesis was stereoselective intramolecular Diels-Alder reaction for construction of the octahydronaphthalene core structure. Our total synthesis as natural enantiomeric form established the unsettled absolute stereochemistry of the antibiotic.",

keywords = "Biologically active compounds, Diels-Alder reactions, Terpenoids",

author = "Yoshikazu Suzuki and Ryoko Nishimaki and Makoto Ishikawa and Takeshi Murata and Takao, {Ken ichi} and Tadano, {Kin ichi}",

note = "Funding Information: We thank Professor W. Steglich (University of Miinchen) for sending us copies of the spectra of natural mniopetal E. We are grateful to Japan Interaction in Science and Technology Forum (JIST) for financial support.",

year = "1999",

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doi = "10.1016/S0040-4039(99)01631-7",

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T1 - Total synthesis of (-)-mniopetal E, a novel biologically intriguing drimane sesquiterpenoid

AU - Suzuki, Yoshikazu

AU - Nishimaki, Ryoko

AU - Ishikawa, Makoto

AU - Murata, Takeshi

AU - Takao, Ken ichi

AU - Tadano, Kin ichi

N1 - Funding Information: We thank Professor W. Steglich (University of Miinchen) for sending us copies of the spectra of natural mniopetal E. We are grateful to Japan Interaction in Science and Technology Forum (JIST) for financial support.

PY - 1999/10/29

Y1 - 1999/10/29

N2 - Total synthesis of (-)-mniopetal E, the common skeleton of the biologically intriguing mniopetals A-D, was accomplished for the first time. The key step of the total synthesis was stereoselective intramolecular Diels-Alder reaction for construction of the octahydronaphthalene core structure. Our total synthesis as natural enantiomeric form established the unsettled absolute stereochemistry of the antibiotic.

AB - Total synthesis of (-)-mniopetal E, the common skeleton of the biologically intriguing mniopetals A-D, was accomplished for the first time. The key step of the total synthesis was stereoselective intramolecular Diels-Alder reaction for construction of the octahydronaphthalene core structure. Our total synthesis as natural enantiomeric form established the unsettled absolute stereochemistry of the antibiotic.

KW - Biologically active compounds

KW - Diels-Alder reactions

KW - Terpenoids

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