A new approach to the synthesis of cyclic ethers via the intermolecular allylation of α-acetoxy ethers and ring-closing metathesis

Isao Kadota; Hiroshi Uyehara; Yoshinori Yamamoto

doi:10.1016/j.tet.2004.05.045

A new approach to the synthesis of cyclic ethers via the intermolecular allylation of α-acetoxy ethers and ring-closing metathesis

Isao Kadota, Hiroshi Uyehara, Yoshinori Yamamoto

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

26 Citations (Scopus)

Abstract

A concise synthesis of the isolaurepinnacin skeleton 6 was achieved via the intermolecular allylation of the α-acetoxy ether 3 followed by ring-closing metathesis. This methodology was successfully applied to the convergent synthesis of the oxocene 15, an advanced synthetic intermediate for the total synthesis of laurencin.

Original language	English
Pages (from-to)	7361-7365
Number of pages	5
Journal	Tetrahedron
Volume	60
Issue number	34
DOIs	https://doi.org/10.1016/j.tet.2004.05.045
Publication status	Published - Aug 16 2004
Externally published	Yes

Keywords

Allylation
Lewis acid
Marine natural product
Polycyclic ether
RCM

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2004.05.045

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title = "A new approach to the synthesis of cyclic ethers via the intermolecular allylation of α-acetoxy ethers and ring-closing metathesis",

abstract = "A concise synthesis of the isolaurepinnacin skeleton 6 was achieved via the intermolecular allylation of the α-acetoxy ether 3 followed by ring-closing metathesis. This methodology was successfully applied to the convergent synthesis of the oxocene 15, an advanced synthetic intermediate for the total synthesis of laurencin.",

keywords = "Allylation, Lewis acid, Marine natural product, Polycyclic ether, RCM",

author = "Isao Kadota and Hiroshi Uyehara and Yoshinori Yamamoto",

note = "Funding Information: This work was financially supported by the Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan.",

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T1 - A new approach to the synthesis of cyclic ethers via the intermolecular allylation of α-acetoxy ethers and ring-closing metathesis

AU - Kadota, Isao

AU - Uyehara, Hiroshi

AU - Yamamoto, Yoshinori

N1 - Funding Information: This work was financially supported by the Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

PY - 2004/8/16

Y1 - 2004/8/16

N2 - A concise synthesis of the isolaurepinnacin skeleton 6 was achieved via the intermolecular allylation of the α-acetoxy ether 3 followed by ring-closing metathesis. This methodology was successfully applied to the convergent synthesis of the oxocene 15, an advanced synthetic intermediate for the total synthesis of laurencin.

AB - A concise synthesis of the isolaurepinnacin skeleton 6 was achieved via the intermolecular allylation of the α-acetoxy ether 3 followed by ring-closing metathesis. This methodology was successfully applied to the convergent synthesis of the oxocene 15, an advanced synthetic intermediate for the total synthesis of laurencin.

KW - Allylation

KW - Lewis acid

KW - Marine natural product

KW - Polycyclic ether

KW - RCM

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VL - 60

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EP - 7365

JO - Tetrahedron

JF - Tetrahedron

IS - 34

ER -

A new approach to the synthesis of cyclic ethers via the intermolecular allylation of α-acetoxy ethers and ring-closing metathesis

Abstract

Keywords

ASJC Scopus subject areas

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