Synthetic Studies on Presporolide, a Putative Enediyne Precursor of Sporolides

Shuji Yamashita; Kanae Terayama; Eri Ozeki; Yujiro Hayashi; Masahiro Hirama

doi:10.1021/acs.orglett.7b03670

Synthetic Studies on Presporolide, a Putative Enediyne Precursor of Sporolides

Shuji Yamashita, Kanae Terayama, Eri Ozeki, Yujiro Hayashi, Masahiro Hirama

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

1 Citation (Scopus)

Abstract

A synthesis of the core framework of presporolide, which possesses both a strained bicyclo[7.3.0]dodecadiyne moiety and a distinctive macrolactone structure, is reported. This synthesis features: (i) a Cu-mediated O-arylation of a hindered tertiary alcohol using triarylbismuth reagent; (ii) stereoselective construction of the strained nine-membered diyne ring; and (iii) atroposelective formation of the macrolactone.

Original language	English
Pages (from-to)	276-279
Number of pages	4
Journal	Organic letters
Volume	20
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.7b03670
Publication status	Published - 2018 Jan 5
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthetic Studies on Presporolide, a Putative Enediyne Precursor of Sporolides",

abstract = "A synthesis of the core framework of presporolide, which possesses both a strained bicyclo[7.3.0]dodecadiyne moiety and a distinctive macrolactone structure, is reported. This synthesis features: (i) a Cu-mediated O-arylation of a hindered tertiary alcohol using triarylbismuth reagent; (ii) stereoselective construction of the strained nine-membered diyne ring; and (iii) atroposelective formation of the macrolactone.",

author = "Shuji Yamashita and Kanae Terayama and Eri Ozeki and Yujiro Hayashi and Masahiro Hirama",

note = "Funding Information: This work was supported financially by JSPS KAKENHI Grant No. 24590003, a Grant-in-Aid for Specially Promoted Research from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), a SUNBOR GRANT from the Suntory Institute for Bioorganic Research, and by a grant from the NOVARTIS Foundation (Japan) for the Promotion of Science (No. 12-106). Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acs.orglett.7b03670",

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AU - Yamashita, Shuji

AU - Terayama, Kanae

AU - Ozeki, Eri

AU - Hayashi, Yujiro

AU - Hirama, Masahiro

N1 - Funding Information: This work was supported financially by JSPS KAKENHI Grant No. 24590003, a Grant-in-Aid for Specially Promoted Research from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), a SUNBOR GRANT from the Suntory Institute for Bioorganic Research, and by a grant from the NOVARTIS Foundation (Japan) for the Promotion of Science (No. 12-106). Publisher Copyright: © 2017 American Chemical Society.

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N2 - A synthesis of the core framework of presporolide, which possesses both a strained bicyclo[7.3.0]dodecadiyne moiety and a distinctive macrolactone structure, is reported. This synthesis features: (i) a Cu-mediated O-arylation of a hindered tertiary alcohol using triarylbismuth reagent; (ii) stereoselective construction of the strained nine-membered diyne ring; and (iii) atroposelective formation of the macrolactone.

AB - A synthesis of the core framework of presporolide, which possesses both a strained bicyclo[7.3.0]dodecadiyne moiety and a distinctive macrolactone structure, is reported. This synthesis features: (i) a Cu-mediated O-arylation of a hindered tertiary alcohol using triarylbismuth reagent; (ii) stereoselective construction of the strained nine-membered diyne ring; and (iii) atroposelective formation of the macrolactone.

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Synthetic Studies on Presporolide, a Putative Enediyne Precursor of Sporolides

Abstract

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