A new synthetic route for construction of the core of Zaragozic acids

Haruta Koshimizu; Tomo Baba; Takehiko Yoshimitsu; Hiroto Nagaoka

doi:10.1016/S0040-4039(99)00256-7

A new synthetic route for construction of the core of Zaragozic acids

Haruta Koshimizu, Tomo Baba, Takehiko Yoshimitsu, Hiroto Nagaoka

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

26 Citations (Scopus)

Abstract

A new synthetic route for construction of the core moiety of zaragozic acids from 2,5-furandimethanol (2) is described. This synthesis involves highly stereocontrolled transformation of 2 into 7-oxabicyclo[2.2.1]heptane derivative 13, and the Grob fragmentation-reduction-iodo acetalization reaction (one-pot process) of 13 as a key step to give 16.

Original language	English
Pages (from-to)	2777-2780
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	14
DOIs	https://doi.org/10.1016/S0040-4039(99)00256-7
Publication status	Published - Apr 2 1999
Externally published	Yes

Keywords

Diels-Alder reactions
Fragmentation reactions
Furans
Zaragozic acids

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(99)00256-7

Cite this

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title = "A new synthetic route for construction of the core of Zaragozic acids",

abstract = "A new synthetic route for construction of the core moiety of zaragozic acids from 2,5-furandimethanol (2) is described. This synthesis involves highly stereocontrolled transformation of 2 into 7-oxabicyclo[2.2.1]heptane derivative 13, and the Grob fragmentation-reduction-iodo acetalization reaction (one-pot process) of 13 as a key step to give 16.",

keywords = "Diels-Alder reactions, Fragmentation reactions, Furans, Zaragozic acids",

author = "Haruta Koshimizu and Tomo Baba and Takehiko Yoshimitsu and Hiroto Nagaoka",

note = "Funding Information: Acknowledgment: This work was supported in part by Grant-in Aid for Scientific Research from the Ministry of Education, Science, Sports and Culture, Japan, and the Science Research Promotion Fund from the Promotion and Mutual Aid Corporation for Private Schools of Japan.",

year = "1999",

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T1 - A new synthetic route for construction of the core of Zaragozic acids

AU - Koshimizu, Haruta

AU - Baba, Tomo

AU - Yoshimitsu, Takehiko

AU - Nagaoka, Hiroto

N1 - Funding Information: Acknowledgment: This work was supported in part by Grant-in Aid for Scientific Research from the Ministry of Education, Science, Sports and Culture, Japan, and the Science Research Promotion Fund from the Promotion and Mutual Aid Corporation for Private Schools of Japan.

PY - 1999/4/2

Y1 - 1999/4/2

N2 - A new synthetic route for construction of the core moiety of zaragozic acids from 2,5-furandimethanol (2) is described. This synthesis involves highly stereocontrolled transformation of 2 into 7-oxabicyclo[2.2.1]heptane derivative 13, and the Grob fragmentation-reduction-iodo acetalization reaction (one-pot process) of 13 as a key step to give 16.

AB - A new synthetic route for construction of the core moiety of zaragozic acids from 2,5-furandimethanol (2) is described. This synthesis involves highly stereocontrolled transformation of 2 into 7-oxabicyclo[2.2.1]heptane derivative 13, and the Grob fragmentation-reduction-iodo acetalization reaction (one-pot process) of 13 as a key step to give 16.

KW - Diels-Alder reactions

KW - Fragmentation reactions

KW - Furans

KW - Zaragozic acids

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

A new synthetic route for construction of the core of Zaragozic acids

Abstract

Keywords

ASJC Scopus subject areas

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