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Synthesis of fused-ring and attached-ring bis-tetrahydrofurans via Pd-catalyzed carboetherification
1Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, USA.
Abstract:
A five step-synthesis of fused bis-tetrahydrofurans and attached bis-tetrahydrofurans from butadiene diepoxide is described. Two sequential Pd-catalyzed carboetherification reactions between protected 1,2-diols and aryl/alkenyl bromides, each of which form both a C-O bond and a C-C bond, are used to generate the heterocyclic rings with >20:1 dr. Installation of different R(1) and R(2) groups is achieved in a straightforward fashion through use of different aryl or alkenyl bromide coupling partners.
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