Synthetic studies directed toward amphidinol 2: elucidation of the relative configuration of the C1–C10 fragment

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Tetrahedron Letters


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*,10S* relative configuration.


Tetrahedron Letters, Volume 49, Issue 43 (October 2008) pp. 6209-6211. DOI: 10.1016/j.tetlet.2008.08.035