Concise and stereocontrolled total syntheses of (+)-castanospermine and N-acetylneuraminic acid methyl ester were achieved from diastereomerically enriched anti, syn, syn-1,3-oxazine and anti, syn, anti-1,3-oxazine, respectively. The key step in this strategy was the stereoselective BF·OEt-mediated allylation.
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| http://dx.doi.org/10.1021/acs.joc.9b00216 | DOI Listing |
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