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].
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Feature-based molecular networking and MS2LDA analysis for the dereplication of adjacent bis-tetrahydrofuran Annonaceous acetogenins.
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Department of Pharmaceutical Sciences, College of Pharmacy, University of Illinois Chicago, Chicago, Illinois, USA.
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Department of Pharmaceutical Sciences, College of Pharmacy, University of Illinois Chicago, Chicago, Illinois 60612, United States.
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College of Pharmacy, Seoul National University Seoul 08826 Korea.
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College of Pharmacy, Seoul National University, Seoul 08826, Korea.
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