Studies on the Synthesis of Gymnodimine. Stereocontrolled Construction of the Tetrahydrofuran Subunit

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...

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Bibliographic Details
Published in:Organic letters 2003-10, Vol.5 (22), p.4109-4112
Main Authors: White, James D, Wang, Guoqiang, Quaranta, Laura
Format: Article
Language:English
Subjects:
Crystallography, X-Ray
Cyclization
Furans - chemistry
Heterocyclic Compounds, 3-Ring - chemical synthesis
Hydrocarbons, Cyclic - chemical synthesis
Imines - chemical synthesis
Iodine - chemistry
Molecular Conformation
Molecular Structure
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol030101c