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

School of Advanced Science and Engineering

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

18 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1518-1522
Number of pages	5
Journal	Tetrahedron Letters
Volume	49
Issue number	9
DOIs	https://doi.org/10.1016/j.tetlet.2007.12.109
Publication status	Published - 2008 Feb 25

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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.",

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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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Synthetic studies on (-)-scabronine A

Abstract

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