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Synthetic studies directed toward amphidinol 2: elucidation of the relative configuration of the C1-C10 fragment
Authors:Praveen Kommana
Institution:Department of Chemistry, Marquette University, PO Box 1881, Milwaukee WI 53201-1881, USA
Abstract:Model compounds (11 and 12) for the C1-C10 tetrahydropyran fragment of amphidinol 2 were prepared from (2S)-benzyloxypropanal in 9 steps. The synthetic route relied on diastereoselective diene-aldehyde cycloaddition, stereoselective C-allylation, and reagent based enantioselective aldehyde allylation. Comparison of the NMR spectra for models 11 and 12 with that for amphidinol 2 indicated that the C1-C10 segment of the natural product possesses the 2R,4R,6R,7S,8R,10Srelative configuration.
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