Total Synthesis of Broussonetine F: The Orthoamide Overman Rearrangement of an Allylic Diol

A first total synthesis of broussonetine F from diethyl l-tartrate was achieved. The cornerstone of our synthesis was an orthoamide Overman rearrangement, which provided an allylic amino alcohol with complete diastereoselectivity.

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Veröffentlicht in:Organic letters 2011-02, Vol.13 (4), p.616-619
Hauptverfasser: Hama, Naoto, Aoki, Toshihiro, Miwa, Shohei, Yamazaki, Miki, Sato, Takaaki, Chida, Noritaka
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Sprache:eng
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Zusammenfassung:A first total synthesis of broussonetine F from diethyl l-tartrate was achieved. The cornerstone of our synthesis was an orthoamide Overman rearrangement, which provided an allylic amino alcohol with complete diastereoselectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol102856j