Synthetic studies of pestalotiopsin A: Asymmetric synthesis of the 2-oxabicyclo[3.2.0]heptane substructure

Ken Ichi Takao; Hiroshi Saegusa; Tomohiro Tsujita; Takenori Washizawa; Kin Ichi Tadano

doi:10.1016/j.tetlet.2005.06.133

Synthetic studies of pestalotiopsin A: Asymmetric synthesis of the 2-oxabicyclo[3.2.0]heptane substructure

Ken Ichi Takao, Hiroshi Saegusa, Tomohiro Tsujita, Takenori Washizawa, Kin Ichi Tadano

Department of Applied Chemistry

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

20 Citations (Scopus)

Abstract

A functionalized 2-oxabicyclo[3.2.0]heptan-3-one derivative, possessing all the skeletal carbons of pestalotiopsin A, has been synthesized. For the preparation of intermediary cyclobutane derivatives in enantioenriched form, the Lewis acid-catalyzed [2+2] cycloaddition of N-propiolated Oppolzer's camphorsultam with dimethylketene bis(trimethylsilyl) acetal followed by a stereoselective 1,4-hydride addition/protonation, has been developed.

Original language	English
Pages (from-to)	5815-5818
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	35
DOIs	https://doi.org/10.1016/j.tetlet.2005.06.133
Publication status	Published - 2005 Aug 29

Keywords

Chiral auxiliary
Cyclobutane
[2+2] Cycloaddition

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2005.06.133

Cite this

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title = "Synthetic studies of pestalotiopsin A: Asymmetric synthesis of the 2-oxabicyclo[3.2.0]heptane substructure",

abstract = "A functionalized 2-oxabicyclo[3.2.0]heptan-3-one derivative, possessing all the skeletal carbons of pestalotiopsin A, has been synthesized. For the preparation of intermediary cyclobutane derivatives in enantioenriched form, the Lewis acid-catalyzed [2+2] cycloaddition of N-propiolated Oppolzer's camphorsultam with dimethylketene bis(trimethylsilyl) acetal followed by a stereoselective 1,4-hydride addition/protonation, has been developed.",

keywords = "Chiral auxiliary, Cyclobutane, [2+2] Cycloaddition",

author = "Takao, {Ken Ichi} and Hiroshi Saegusa and Tomohiro Tsujita and Takenori Washizawa and Tadano, {Kin Ichi}",

note = "Funding Information: This work was supported by the Takeda Science Foundation and a Grant-in-Aid for Scientific Research from MEXT, Japan. ",

year = "2005",

month = aug,

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doi = "10.1016/j.tetlet.2005.06.133",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Synthetic studies of pestalotiopsin A

T2 - Asymmetric synthesis of the 2-oxabicyclo[3.2.0]heptane substructure

AU - Takao, Ken Ichi

AU - Saegusa, Hiroshi

AU - Tsujita, Tomohiro

AU - Washizawa, Takenori

AU - Tadano, Kin Ichi

N1 - Funding Information: This work was supported by the Takeda Science Foundation and a Grant-in-Aid for Scientific Research from MEXT, Japan.

PY - 2005/8/29

Y1 - 2005/8/29

N2 - A functionalized 2-oxabicyclo[3.2.0]heptan-3-one derivative, possessing all the skeletal carbons of pestalotiopsin A, has been synthesized. For the preparation of intermediary cyclobutane derivatives in enantioenriched form, the Lewis acid-catalyzed [2+2] cycloaddition of N-propiolated Oppolzer's camphorsultam with dimethylketene bis(trimethylsilyl) acetal followed by a stereoselective 1,4-hydride addition/protonation, has been developed.

AB - A functionalized 2-oxabicyclo[3.2.0]heptan-3-one derivative, possessing all the skeletal carbons of pestalotiopsin A, has been synthesized. For the preparation of intermediary cyclobutane derivatives in enantioenriched form, the Lewis acid-catalyzed [2+2] cycloaddition of N-propiolated Oppolzer's camphorsultam with dimethylketene bis(trimethylsilyl) acetal followed by a stereoselective 1,4-hydride addition/protonation, has been developed.

KW - Chiral auxiliary

KW - Cyclobutane

KW - [2+2] Cycloaddition

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DO - 10.1016/j.tetlet.2005.06.133

M3 - Article

AN - SCOPUS:23044491852

SN - 0040-4039

VL - 46

SP - 5815

EP - 5818

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 35

ER -

Synthetic studies of pestalotiopsin A: Asymmetric synthesis of the 2-oxabicyclo[3.2.0]heptane substructure

Abstract

Keywords

ASJC Scopus subject areas

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