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A reviewer suggested that this alkylation step could be improved through application of a procedure described by Williams and Im for the alkylation of oxazinones in which potassium hexamethyldisilazide in toluene is added at -80 C to a solution of the oxazinone and methyl iodide. Williams, R. M.; Im, M.-N. J. Am. Chem. Soc. 1991, 113,9276. Unfortunately, circumstances did not permit the exploration of this methodology.
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42
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33744649608
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note
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Initial studies of this reaction were conducted with the C7C20 prototype A. The stereochemistry of the derived olefin B was confirmed by the observation of an NOE between the C14 Me and the C16 méthylène.
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