Synthetic studies on (-)-FR182877: construction of the ABCD ring system via the intramolecular cycloadditions (2)

Natsumi Tanaka; Takahiro Suzuki; Yosuke Hosoya; Masahisa Nakada

doi:10.1016/j.tetlet.2007.07.052

Synthetic studies on (-)-FR182877: construction of the ABCD ring system via the intramolecular cycloadditions (2)

Natsumi Tanaka, Takahiro Suzuki, Yosuke Hosoya, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

18 Citations (Scopus)

Abstract

Construction of the ABCD ring system of (-)-FR182877 via the intramolecular Diels-Alder (IMDA) reaction and the highly diastereoselective intramolecular hetero-Diels-Alder (IMHDA) reaction is described. The IMHDA reactions of the substrates incorporating the oxabutadiene with the E- or Z-alkene were examined, revealing that the sole product was obtained from both substrates and the E-alkene geometry was found to be crucial to obtaining the desired product.

Original language	English
Pages (from-to)	6488-6492
Number of pages	5
Journal	Tetrahedron Letters
Volume	48
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2007.07.052
Publication status	Published - 2007 Sept 10

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2007.07.052

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title = "Synthetic studies on (-)-FR182877: construction of the ABCD ring system via the intramolecular cycloadditions (2)",

abstract = "Construction of the ABCD ring system of (-)-FR182877 via the intramolecular Diels-Alder (IMDA) reaction and the highly diastereoselective intramolecular hetero-Diels-Alder (IMHDA) reaction is described. The IMHDA reactions of the substrates incorporating the oxabutadiene with the E- or Z-alkene were examined, revealing that the sole product was obtained from both substrates and the E-alkene geometry was found to be crucial to obtaining the desired product.",

author = "Natsumi Tanaka and Takahiro Suzuki and Yosuke Hosoya and Masahisa Nakada",

note = "Funding Information: This work was financially supported in part by a Waseda University Grant for Special Research Projects and a Grant-in-Aid for Scientific Research (C) and Scientific Research on Priority Areas (Creation of Biologically Functional Molecules (No. 17035082)) from MEXT, Japan. We are also indebted to GCOE {\textquoteleft}Practical Chemical Wisdom{\textquoteright}. ",

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AU - Tanaka, Natsumi

AU - Suzuki, Takahiro

AU - Hosoya, Yosuke

AU - Nakada, Masahisa

N1 - Funding Information: This work was financially supported in part by a Waseda University Grant for Special Research Projects and a Grant-in-Aid for Scientific Research (C) and Scientific Research on Priority Areas (Creation of Biologically Functional Molecules (No. 17035082)) from MEXT, Japan. We are also indebted to GCOE ‘Practical Chemical Wisdom’.

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Synthetic studies on (-)-FR182877: construction of the ABCD ring system via the intramolecular cycloadditions (2)

Abstract

ASJC Scopus subject areas

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