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Formal synthesis of cis-solamin: acid-catalyzed one-step construction of 2,5-disubstituted tetrahydrofuran

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Abstract

A divergent strategy has been used for the concise and efficient enantioselective formal synthesis of Annonaceous acetogenin cis-solamin. Our synthetic strategy comprises concise preparation of the diepoxyester via an 11-membered silaketal constructed by ring-closing metathesis after the dimerization of chiral epoxides, and uses an acid-catalyzed tandem intramolecular SN2-like reaction to construct the threo-cis-threo configuration of the tetrahydrofuran-diol moiety.

Graphical abstract: Formal synthesis of cis-solamin: acid-catalyzed one-step construction of 2,5-disubstituted tetrahydrofuran

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Publication details

The article was received on 10 Mar 2018, accepted on 03 Apr 2018 and first published on 04 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00603B
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Formal synthesis of cis-solamin: acid-catalyzed one-step construction of 2,5-disubstituted tetrahydrofuran

    K. Ota, T. Yamashita, S. Kohno, A. Miura, K. Kamaike and H. Miyaoka, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB00603B

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