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Chemistry ; 19(38): 12649-52, 2013 Sep 16.
Article in English | MEDLINE | ID: mdl-23956022

ABSTRACT

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.


Subject(s)
Biological Products/chemistry , Furans/chemical synthesis , Biological Products/chemical synthesis , Catalysis , Chlorohydrins/chemistry , Furans/chemistry , Halogenation , Laurencia/chemistry , Laurencia/metabolism , Magnetic Resonance Spectroscopy , Stereoisomerism
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