Stereochemically general approach to adjacent bis(tetrahydrofuran) cores of annonaceous acetogenins.

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Organic Letters. 2006 Nov 23;8(24):5637-40. doi: 10.1021/ol062390l

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Wysocki LM, Dodge MW, Voight EA, Burke SD

Note: Research in this publication was not performed at Janelia.

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Abstract

A series of six 2,5-disubstituted adjacent bis(tetrahydrofuran) stereoisomers with trans/erythro/cis, trans/threo/trans, or cis/threo/cis relative stereochemistry have been synthesized from known dihydroxycyclooctenes via ring opening/cross metathesis and Pd(0)-mediated asymmetric double cycloetherification. The stereochemistry of four of these isomers has been found in the biologically active annonaceous acetogenin natural products. [reaction: see text].

PMID: 17107091 [PubMed - indexed for MEDLINE]

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Stereochemically general approach to adjacent bis(tetrahydrofuran) cores of annonaceous acetogenins.

Note: Research in this publication was not performed at Janelia.

Abstract

PMID: 17107091 [PubMed - indexed for MEDLINE]

Janelia Authors