Synthetic studies on (-)-scabronine A

Hideaki Watanabe; Masahisa Nakada

doi:10.1016/j.tetlet.2007.12.109

Synthetic studies on (-)-scabronine A

Hideaki Watanabe, Masahisa Nakada^*

^*この研究の対応する著者

先進理工学部

研究成果: Article › 査読

18 被引用数 (Scopus)

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This Letter describes synthetic studies on (-)-scabronine A utilizing a new chiral building block successfully prepared via the catalytic asymmetric intramolecular cyclopropanation (IMCP) of an α-diazo-β-keto sulfone. The crucial transformations in this study are the coupling reaction of two fragments between the positions adjacent to a quaternary carbon center, the intramolecular aldol reaction, the C14 hydroxyl-directed hydrogenation, and the ring-expansion reaction to furnish the 5-6-7 tricyclic cyathane skeleton.

本文言語	English
ページ（範囲）	1518-1522
ページ数	5
ジャーナル	Tetrahedron Letters
巻	49
号	9
DOI	https://doi.org/10.1016/j.tetlet.2007.12.109
出版ステータス	Published - 2008 2月 25

ASJC Scopus subject areas

生化学
創薬
有機化学

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10.1016/j.tetlet.2007.12.109

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title = "Synthetic studies on (-)-scabronine A",

abstract = "This Letter describes synthetic studies on (-)-scabronine A utilizing a new chiral building block successfully prepared via the catalytic asymmetric intramolecular cyclopropanation (IMCP) of an α-diazo-β-keto sulfone. The crucial transformations in this study are the coupling reaction of two fragments between the positions adjacent to a quaternary carbon center, the intramolecular aldol reaction, the C14 hydroxyl-directed hydrogenation, and the ring-expansion reaction to furnish the 5-6-7 tricyclic cyathane skeleton.",

author = "Hideaki Watanabe and Masahisa Nakada",

note = "Funding Information: This work was financially supported in part by a Waseda University Grant for Special Research Projects, a Grant-in-Aid for Scientific Research on Priority Areas (Creation of Biologically Functional Molecules (No. 17035082)), Young Scientists (start-up research (No. 18850023)), and the Global COE program {\textquoteleft}Center for Practical Chemical Wisdom{\textquoteright} of MEXT.",

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AU - Nakada, Masahisa

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N2 - This Letter describes synthetic studies on (-)-scabronine A utilizing a new chiral building block successfully prepared via the catalytic asymmetric intramolecular cyclopropanation (IMCP) of an α-diazo-β-keto sulfone. The crucial transformations in this study are the coupling reaction of two fragments between the positions adjacent to a quaternary carbon center, the intramolecular aldol reaction, the C14 hydroxyl-directed hydrogenation, and the ring-expansion reaction to furnish the 5-6-7 tricyclic cyathane skeleton.

AB - This Letter describes synthetic studies on (-)-scabronine A utilizing a new chiral building block successfully prepared via the catalytic asymmetric intramolecular cyclopropanation (IMCP) of an α-diazo-β-keto sulfone. The crucial transformations in this study are the coupling reaction of two fragments between the positions adjacent to a quaternary carbon center, the intramolecular aldol reaction, the C14 hydroxyl-directed hydrogenation, and the ring-expansion reaction to furnish the 5-6-7 tricyclic cyathane skeleton.

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JO - Tetrahedron Letters

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Synthetic studies on (-)-scabronine A

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