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Chemistry. 2013 Sep 16;19(38):12649-52. doi: 10.1002/chem.201302352. Epub 2013 Aug 19.

Total synthesis and structural revision of laurefurenynes A and B.

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  • 1Department of Chemistry, Simon Fraser University, Burnaby, V5A 1S6, BC (Canada), Fax: (+1) 1-778-782-3765.


Structural reassignment: 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 (1) H NMR spectra of synthetic and natural material led to a configurational reassignment for the natural product, which was also confirmed by total synthesis.

Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


chlorohydrin; laurefurenyne A; laurencia acetogenins; organocatalysis; total synthesis

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