Stereoselective Syntheses of all the Possible Stereoisomers of Coronafacic Acid

Raku Watanabe; Nobuki Kato; Kengo Hayashi; Sho Tozawa; Yusuke Ogura; Shigefumi Kuwahara; Minoru Ueda

doi:10.1002/open.202000210

Stereoselective Syntheses of all the Possible Stereoisomers of Coronafacic Acid

Raku Watanabe, Nobuki Kato, Kengo Hayashi, Sho Tozawa, Yusuke Ogura, Shigefumi Kuwahara, Minoru Ueda

SCI - Chemistry

Tohoku University

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

2 Citations (Scopus)

Abstract

An efficient and stereoselective syntheses of all the possible stereoisomers of coronafacic acid (CFA) has been developed. The stereochemistries of C3a and C7a were controlled in a diastereoselective Diels-Alder type cycloaddition using a chiral auxiliary. CFA and 6-epi-CFA were synthesized by hydrogenation of a common intermediate. During the synthesis of 6-epi-CFA, we established that its cis-fused configuration is important for the introduction of C4-C5 double bond by dehydration. This report is the first practical synthesis of both 6-epi-CFA, and its enantiomer.

Original language	English
Pages (from-to)	1008-1017
Number of pages	10
Journal	ChemistryOpen
Volume	9
Issue number	10
DOIs	https://doi.org/10.1002/open.202000210
Publication status	Published - 2020 Oct 1

Keywords

coronatine
natural products
phytochemistry

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10.1002/open.202000210

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abstract = "An efficient and stereoselective syntheses of all the possible stereoisomers of coronafacic acid (CFA) has been developed. The stereochemistries of C3a and C7a were controlled in a diastereoselective Diels-Alder type cycloaddition using a chiral auxiliary. CFA and 6-epi-CFA were synthesized by hydrogenation of a common intermediate. During the synthesis of 6-epi-CFA, we established that its cis-fused configuration is important for the introduction of C4-C5 double bond by dehydration. This report is the first practical synthesis of both 6-epi-CFA, and its enantiomer.",

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author = "Raku Watanabe and Nobuki Kato and Kengo Hayashi and Sho Tozawa and Yusuke Ogura and Shigefumi Kuwahara and Minoru Ueda",

note = "Funding Information: This work was financially supported by a Grant‐in‐Aid for Scientific Research for MU from JSPS, Japan (nos. 17H06407, 18KK0162, and 20H00402), JSPS A3 Foresight Program (MU), and JSPS Core‐to‐Core Program Asian Chemical Biology Initiative (MU), for NK (no. 19K06968), SUNBOR GRANT (NK). Publisher Copyright: {\textcopyright} 2020 The Authors. Published by Wiley-VCH GmbH",

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doi = "10.1002/open.202000210",

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AU - Watanabe, Raku

AU - Kato, Nobuki

AU - Hayashi, Kengo

AU - Tozawa, Sho

AU - Ogura, Yusuke

AU - Kuwahara, Shigefumi

AU - Ueda, Minoru

N1 - Funding Information: This work was financially supported by a Grant‐in‐Aid for Scientific Research for MU from JSPS, Japan (nos. 17H06407, 18KK0162, and 20H00402), JSPS A3 Foresight Program (MU), and JSPS Core‐to‐Core Program Asian Chemical Biology Initiative (MU), for NK (no. 19K06968), SUNBOR GRANT (NK). Publisher Copyright: © 2020 The Authors. Published by Wiley-VCH GmbH

PY - 2020/10/1

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N2 - An efficient and stereoselective syntheses of all the possible stereoisomers of coronafacic acid (CFA) has been developed. The stereochemistries of C3a and C7a were controlled in a diastereoselective Diels-Alder type cycloaddition using a chiral auxiliary. CFA and 6-epi-CFA were synthesized by hydrogenation of a common intermediate. During the synthesis of 6-epi-CFA, we established that its cis-fused configuration is important for the introduction of C4-C5 double bond by dehydration. This report is the first practical synthesis of both 6-epi-CFA, and its enantiomer.

AB - An efficient and stereoselective syntheses of all the possible stereoisomers of coronafacic acid (CFA) has been developed. The stereochemistries of C3a and C7a were controlled in a diastereoselective Diels-Alder type cycloaddition using a chiral auxiliary. CFA and 6-epi-CFA were synthesized by hydrogenation of a common intermediate. During the synthesis of 6-epi-CFA, we established that its cis-fused configuration is important for the introduction of C4-C5 double bond by dehydration. This report is the first practical synthesis of both 6-epi-CFA, and its enantiomer.

KW - coronatine

KW - natural products

KW - phytochemistry

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Stereoselective Syntheses of all the Possible Stereoisomers of Coronafacic Acid

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Keywords

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