Journal
ORGANIC LETTERS
Volume 3, Issue 17, Pages 2677-2680Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol0101279
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[GRAPHICS] An efficient and highly stereoselective synthesis of the gastroprotective natural product Al-77-B is described. The stereocenters of the hydroxy amino acid moiety were generated by an ester-derived titanium-enolate-mediated syn-aldol reaction, a Curtius rearrangement, and application of Dondoni's aldehyde homologation. Condensation with the dihydroisocoumarin fragment and subsequent deprotecting transformations furnished optically active Al-77-B.
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