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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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

PY - 1999/10/29

Y1 - 1999/10/29

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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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