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Formal synthesis of: Cis -solamin: Acid-catalyzed one-step construction of 2,5-disubstituted tetrahydrofuran

Organic and Biomolecular Chemistry, ISSN: 1477-0520, Vol: 16, Issue: 16, Page: 3018-3025
2018
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Article Description

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 S2-like reaction to construct the threo-cis-threo configuration of the tetrahydrofuran-diol moiety.

Bibliographic Details

Ota, Koichiro; Yamashita, Tomoko; Kohno, Sumika; Miura, Atsuko; Kamaike, Kazuo; Miyaoka, Hiroaki

Royal Society of Chemistry (RSC)

Biochemistry, Genetics and Molecular Biology; Chemistry

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