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An expeditious route to the synthesis of highly functionalized chiral oxepines from monosaccharides

✍ Scribed by Huib Ovaa; Michiel A Leeuwenburgh; Herman S Overkleeft; Gijs A van der Marel; Jacques H van Boom

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 216 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)00324-4

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✦ Synopsis

The transformation of partially protected aldofuranoses into dienes by Wittig olefination of the anomeric center followed by either allylation or oxopalladation of alkoxy-l,2-propadienes is described. Ring-closing metathesis of the linear dienes gives rise to a variety of highly functionalized and chiral ring-expanded oxepines.

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