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ChemInform Abstract: An Expeditious Route to the Synthesis of Highly Functionalized Chiral Oxepins from Monosaccharides.

✍ Scribed by H. OVAA; M. A. LEEUWENBURGH; H. S. OVERKLEEFT; G. A. VAN DER MAREL; J. H. VAN BOOM

Publisher: John Wiley and Sons
Year: 2010
Weight: 36 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199831171

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✦ Synopsis

An Expeditious Route to the Synthesis of Highly Functionalized Chiral Oxepins from Monosaccharides.

-A novel and versatile route to highly functionalized chiral oxepins [cf. (VI) and (IX)] derived from partially protected aldofuranoses such as (I) is reported. The transformation proceeds via Wittig olefination of the anomeric center followed by allylation or oxopalladation of (III). Ring-closing metathesis of the resulting dienes (V) and (VIII) yields the ring-expanded products. -(OVAA, H.; LEEUWENBURGH,

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