Pd-catalyzed Regio- A nd Stereoselective Hydrostannylation of an Alkyl Ethynyl Ether/One-Pot Stille Coupling Enables the Synthesis of 14-Membered Macrolactone of Luminamicin

Akihiro Sugawara; Hirokazu Takada; Tomoyasu Hirose; Aoi Kimishima; Takeshi Yamada; Masaki Toda; Toru Kojima; Takanori Matsumaru; Toshiaki Sunazuka

doi:10.1021/acs.orglett.1c00183

Pd-catalyzed Regio- A nd Stereoselective Hydrostannylation of an Alkyl Ethynyl Ether/One-Pot Stille Coupling Enables the Synthesis of 14-Membered Macrolactone of Luminamicin

Akihiro Sugawara, Hirokazu Takada, Tomoyasu Hirose, Aoi Kimishima, Takeshi Yamada, Masaki Toda, Toru Kojima, Takanori Matsumaru, Toshiaki Sunazuka

研究成果: Article › 査読

2 被引用数 (Scopus)

抄録

Regio- A nd stereoselective hydrostannylation of alkyl ethynyl ethers generates alkenyl ethers, which are useful building blocks in organic synthesis. This efficient synthetic method, however, is limited. Here, we report not only an efficient method for a highly regio- A nd stereoselective Pd-catalyzed hydrostannylation of alkyl ethynyl ethers but also a scalable synthesis and construction of the core framework of luminamicin possessing all functional groups and stereocenters.

本文言語	English
ページ（範囲）	1758-1763
ページ数	6
ジャーナル	Organic Letters
巻	23
号	5
DOI	https://doi.org/10.1021/acs.orglett.1c00183
出版ステータス	Published - 2021 3月 5
外部発表	はい

ASJC Scopus subject areas

生化学
物理化学および理論化学
有機化学

文献へのアクセス

10.1021/acs.orglett.1c00183

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フィンガープリント

「Pd-catalyzed Regio- A nd Stereoselective Hydrostannylation of an Alkyl Ethynyl Ether/One-Pot Stille Coupling Enables the Synthesis of 14-Membered Macrolactone of Luminamicin」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル

Sugawara, A., Takada, H., Hirose, T., Kimishima, A., Yamada, T., Toda, M., Kojima, T., Matsumaru, T., & Sunazuka, T. (2021). Pd-catalyzed Regio- A nd Stereoselective Hydrostannylation of an Alkyl Ethynyl Ether/One-Pot Stille Coupling Enables the Synthesis of 14-Membered Macrolactone of Luminamicin. Organic Letters, 23(5), 1758-1763. https://doi.org/10.1021/acs.orglett.1c00183

Sugawara, A, Takada, H, Hirose, T, Kimishima, A, Yamada, T, Toda, M, Kojima, T, Matsumaru, T & Sunazuka, T 2021, 'Pd-catalyzed Regio- A nd Stereoselective Hydrostannylation of an Alkyl Ethynyl Ether/One-Pot Stille Coupling Enables the Synthesis of 14-Membered Macrolactone of Luminamicin', Organic Letters, vol. 23, no. 5, pp. 1758-1763. https://doi.org/10.1021/acs.orglett.1c00183

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abstract = "Regio- A nd stereoselective hydrostannylation of alkyl ethynyl ethers generates alkenyl ethers, which are useful building blocks in organic synthesis. This efficient synthetic method, however, is limited. Here, we report not only an efficient method for a highly regio- A nd stereoselective Pd-catalyzed hydrostannylation of alkyl ethynyl ethers but also a scalable synthesis and construction of the core framework of luminamicin possessing all functional groups and stereocenters. ",

author = "Akihiro Sugawara and Hirokazu Takada and Tomoyasu Hirose and Aoi Kimishima and Takeshi Yamada and Masaki Toda and Toru Kojima and Takanori Matsumaru and Toshiaki Sunazuka",

note = "Funding Information: We are grateful to Distinguished Emeritus Professor Satoshi O̅mura (Kitasato University) for his helpful support and valuable suggestions. This work was supported by Japan Society for the Promotion of Science (JSPS) KAKENHI grants (Nos. 16K08175, 26860015, 24790022, 22890175 (A.S.), and 18K06586 (T.H.)), a Meiji Seika Pharma Award in Synthetic Organic Chemistry Japan (A.S.); a Kitasato University Research Grant for Young Researchers (A.S.), JSPS Research Fellowships for Young Scientists (T.M. and A.K.), and a Uehara Memorial foundation grant (T.H.). This research was also partially supported by Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED under Grant No. JP20am0101096 and AMED under Grant No. 20ae0101047. We also thank Dr. K. Nagai and Ms. N. Sato (School of Pharmacy, Kitasato University) for their analyses of mass and NMR spectra. Publisher Copyright: {\textcopyright} 2021 American Chemical Society. All rights reserved.",

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AU - Sugawara, Akihiro

AU - Takada, Hirokazu

AU - Hirose, Tomoyasu

AU - Kimishima, Aoi

AU - Yamada, Takeshi

AU - Toda, Masaki

AU - Kojima, Toru

AU - Matsumaru, Takanori

AU - Sunazuka, Toshiaki

N1 - Funding Information: We are grateful to Distinguished Emeritus Professor Satoshi O̅mura (Kitasato University) for his helpful support and valuable suggestions. This work was supported by Japan Society for the Promotion of Science (JSPS) KAKENHI grants (Nos. 16K08175, 26860015, 24790022, 22890175 (A.S.), and 18K06586 (T.H.)), a Meiji Seika Pharma Award in Synthetic Organic Chemistry Japan (A.S.); a Kitasato University Research Grant for Young Researchers (A.S.), JSPS Research Fellowships for Young Scientists (T.M. and A.K.), and a Uehara Memorial foundation grant (T.H.). This research was also partially supported by Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED under Grant No. JP20am0101096 and AMED under Grant No. 20ae0101047. We also thank Dr. K. Nagai and Ms. N. Sato (School of Pharmacy, Kitasato University) for their analyses of mass and NMR spectra. Publisher Copyright: © 2021 American Chemical Society. All rights reserved.

PY - 2021/3/5

Y1 - 2021/3/5

N2 - Regio- A nd stereoselective hydrostannylation of alkyl ethynyl ethers generates alkenyl ethers, which are useful building blocks in organic synthesis. This efficient synthetic method, however, is limited. Here, we report not only an efficient method for a highly regio- A nd stereoselective Pd-catalyzed hydrostannylation of alkyl ethynyl ethers but also a scalable synthesis and construction of the core framework of luminamicin possessing all functional groups and stereocenters.

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