Synthesis of a truncated analog of amphidinol 3 corresponding to the C21C39/C52C67 section

Makoto Ebine; Yuri Takada; Naoto Yanai; Tohru Oishi

doi:10.1246/cl.170050

Synthesis of a truncated analog of amphidinol 3 corresponding to the C21C39/C52C67 section

Makoto Ebine, Yuri Takada, Naoto Yanai, Tohru Oishi

Organic and Biological Chemistry

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

9 Citations (Scopus)

Abstract

As a part of structureactivity relationship studies to elucidate structure requirements for eliciting antifungal activity, an artificial analog of amphidinol 3 (AM3) was designed. A truncated analog corresponding to the C21C39/C52C67 section was synthesized by using SuzukiMiyaura coupling and JuliaKocienski olefination as key steps. An expeditious and versatile method to construct the C53C67 polyene section was also developed based on a linchpin strategy via successive cross-coupling reactions. The analog elicited no antifungal activity, suggesting that the two tetrahydropyran rings of AM3 are necessary to elicit antifungal activity.

Original language	English
Pages (from-to)	662-664
Number of pages	3
Journal	Chemistry Letters
Volume	46
Issue number	5
DOIs	https://doi.org/10.1246/cl.170050
Publication status	Published - 2017

All Science Journal Classification (ASJC) codes

Chemistry(all)

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10.1246/cl.170050

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title = "Synthesis of a truncated analog of amphidinol 3 corresponding to the C21C39/C52C67 section",

abstract = "As a part of structureactivity relationship studies to elucidate structure requirements for eliciting antifungal activity, an artificial analog of amphidinol 3 (AM3) was designed. A truncated analog corresponding to the C21C39/C52C67 section was synthesized by using SuzukiMiyaura coupling and JuliaKocienski olefination as key steps. An expeditious and versatile method to construct the C53C67 polyene section was also developed based on a linchpin strategy via successive cross-coupling reactions. The analog elicited no antifungal activity, suggesting that the two tetrahydropyran rings of AM3 are necessary to elicit antifungal activity.",

author = "Makoto Ebine and Yuri Takada and Naoto Yanai and Tohru Oishi",

note = "Funding Information: We are grateful to Dr. Yukihiro Tashiro, Faculty of Agriculture, Kyushu University for helpful discussion on antifungal activity. This work was supported in part by: i) a fund from Kyushu University, Funds for the Development of Human Resources in Science and Technology originating from MEXT, ii) JST ERATO Lipid Active Structure, and iii) JSPS KAKENHI Grant Numbers JP24750092, JP15K17857, JP15K13645, and JP16H01159 in Middle Molecular Strategy. Publisher Copyright: {\textcopyright} 2017 The Chemical Society of Japan.",

year = "2017",

doi = "10.1246/cl.170050",

language = "English",

volume = "46",

pages = "662--664",

journal = "Chemistry Letters",

issn = "0366-7022",

publisher = "The Chemical Society of Japan",

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TY - JOUR

T1 - Synthesis of a truncated analog of amphidinol 3 corresponding to the C21C39/C52C67 section

AU - Ebine, Makoto

AU - Takada, Yuri

AU - Yanai, Naoto

AU - Oishi, Tohru

N1 - Funding Information: We are grateful to Dr. Yukihiro Tashiro, Faculty of Agriculture, Kyushu University for helpful discussion on antifungal activity. This work was supported in part by: i) a fund from Kyushu University, Funds for the Development of Human Resources in Science and Technology originating from MEXT, ii) JST ERATO Lipid Active Structure, and iii) JSPS KAKENHI Grant Numbers JP24750092, JP15K17857, JP15K13645, and JP16H01159 in Middle Molecular Strategy. Publisher Copyright: © 2017 The Chemical Society of Japan.

PY - 2017

Y1 - 2017

N2 - As a part of structureactivity relationship studies to elucidate structure requirements for eliciting antifungal activity, an artificial analog of amphidinol 3 (AM3) was designed. A truncated analog corresponding to the C21C39/C52C67 section was synthesized by using SuzukiMiyaura coupling and JuliaKocienski olefination as key steps. An expeditious and versatile method to construct the C53C67 polyene section was also developed based on a linchpin strategy via successive cross-coupling reactions. The analog elicited no antifungal activity, suggesting that the two tetrahydropyran rings of AM3 are necessary to elicit antifungal activity.

AB - As a part of structureactivity relationship studies to elucidate structure requirements for eliciting antifungal activity, an artificial analog of amphidinol 3 (AM3) was designed. A truncated analog corresponding to the C21C39/C52C67 section was synthesized by using SuzukiMiyaura coupling and JuliaKocienski olefination as key steps. An expeditious and versatile method to construct the C53C67 polyene section was also developed based on a linchpin strategy via successive cross-coupling reactions. The analog elicited no antifungal activity, suggesting that the two tetrahydropyran rings of AM3 are necessary to elicit antifungal activity.

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ER -

Synthesis of a truncated analog of amphidinol 3 corresponding to the C21C39/C52C67 section

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