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

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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)7835-7838
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number44
DOIs
Publication statusPublished - 1999 Oct 29

Fingerprint

Cycloaddition Reaction
Skeleton
Anti-Bacterial Agents
Stereochemistry
drimane
mniopetal E

Keywords

  • Biologically active compounds
  • Diels-Alder reactions
  • Terpenoids

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Total synthesis of (-)-mniopetal E, a novel biologically intriguing drimane sesquiterpenoid. / Suzuki, Yoshikazu; Nishimaki, Ryoko; Ishikawa, Makoto; Murata, Takeshi; Takao, Kenichi; Tadano, Kin ichi.

In: Tetrahedron Letters, Vol. 40, No. 44, 29.10.1999, p. 7835-7838.

Research output: Contribution to journalArticle

Suzuki, Yoshikazu ; Nishimaki, Ryoko ; Ishikawa, Makoto ; Murata, Takeshi ; Takao, Kenichi ; Tadano, Kin ichi. / Total synthesis of (-)-mniopetal E, a novel biologically intriguing drimane sesquiterpenoid. In: Tetrahedron Letters. 1999 ; Vol. 40, No. 44. pp. 7835-7838.
@article{2fff0e2d742f401a86c05200a3d8d31f,
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 Kenichi Takao and Tadano, {Kin ichi}",
year = "1999",
month = "10",
day = "29",
doi = "10.1016/S0040-4039(99)01631-7",
language = "English",
volume = "40",
pages = "7835--7838",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "44",

}

TY - JOUR

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, Kenichi

AU - Tadano, Kin ichi

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

UR - http://www.scopus.com/inward/record.url?scp=0033615781&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033615781&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(99)01631-7

DO - 10.1016/S0040-4039(99)01631-7

M3 - Article

VL - 40

SP - 7835

EP - 7838

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 44

ER -