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  • Title: Studies on the synthesis of gymnodimine. Stereocontrolled construction of the tetrahydrofuran subunit.
    Author: White JD, Wang G, Quaranta L.
    Journal: Org Lett; 2003 Oct 30; 5(22):4109-12. PubMed ID: 14572261.
    Abstract:
    [reaction: see text]. A bis-(2,6-dichlorobenzyl) ether is shown to undergo efficient and highly stereoselective intramolecular iodoetherification to yield a cis-2,5-disubstituted tetrahydrofuran, thus providing a powerful illustration of a stereodirecting effect first noted by Rychnovsky and Bartlett. The tetrahydrofuran was transformed into a subunit suitable for incorporation into the shellfish toxin gymnodimine.
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