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Stereoselective Construction of cis -2,6-Disubstituted Tetrahydropyrans via the Reductive Etherification of δ-Trialkylsilyloxy Substituted Ketones: Total Synthesis of (−)-Centrolobine

✍ Scribed by Evans, P. Andrew; Cui, Jian; Gharpure, Santosh J.

Book ID: 127167684
Publisher: American Chemical Society
Year: 2003
Tongue: English
Weight: 70 KB
Volume: 5
Category: Article
ISSN: 1523-7060
DOI: 10.1021/ol035438t

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✍ P. Andrew Evans; Jian Cui; Santosh J. Gharpure 📂 Article 📅 2004 🏛 John Wiley and Sons ⚖ 215 KB 👁 2 views

Diastereoselective construction of cis 2

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Diastereoselective construction of 2,6-disubstituted tetrahydropyrans with an exocyclic double bond was achieved via the In(OTf) 3 -catalyzed intramolecular 2,5-oxonium-ene cyclization. Its application was further demonstrated by the synthesis of a common intermediate for both zampanolide and dactyl

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