Stereochemically General Approach to Adjacent Bis(tetrahydrofuran) Cores of Annonaceous Acetogenins
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A series of six 2,5-disubstituted adjacent bis(tetrahydrofuran) stereoisomers with trans/erythro/cis, trans/threo/trans, or cis/threo/cis relativestereochemistry have been synthesized from known dihydroxycyclooctenes via ring opening/cross metathesis and Pd(0)-mediated asymmetricdouble cycloetherification. The stereochemistry of four of these isomers has been found in the biologically active annonaceous acetogeninnatural products.

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