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

✍ Scribed by Praveen Kommana; Seung Won Chung; William A. Donaldson

Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 205 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.08.035

No coin nor oath required. For personal study only.

✦ Synopsis

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.

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