Total Synthesis and Structural Revision of Laurefurenynes A and B. Issue 38 (19th August 2013)

• Record Type: Journal Article
• Authors: Holmes, Michael T.; Britton, Robert
• Is Part Of: Chemistry. Volume 19:Issue 38(2013)
• Page Start: 12649
• Page End: 12652
• Publication Date: 2013-08-19
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201302352
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>Structural reassignment</bold>: A total synthesis of the proposed structure of (−)‐laurefurenyne A has been accomplished that relies on organocatalytic aldehyde α‐chlorination and a flexible chlorohydrin‐based strategy for stereocontrolled access to the bis‐tetrahydrofuran core of the natural product. Analysis of incongruities between the ¹H NMR spectra of synthetic and natural material led to a configurational reassignment for the natural product, which was also confirmed by total synthesis.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg37rmp5jx" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>