Of destomic acid

A. Golebiowski, J. Kozak, and i. Jurczack, Syntheses of destomic acid and anhydrogalantinic acid from L-serinal, J. Org. Chem. 5t5 7344 (1991). 

SCHEME 13.65 Marshall s allylation applied to the synthesis of destomic acid. Copyright 2006 by Taylor Francis Group LLC... 

Marshall s allylatlon applied to the synthesis of destomic acid... 

During the synthesis of destomic acid derivatives, Hashimoto et al. reported successful cleavage of A -benzyloxycarbonylated 6,7-epimino heptopyranosides 432-433 with acetic acid under heating. The cleavage reactions regioselectively gave 7-acetoxy derivatives 434-435 in high yields (98 and 88%). 

Further examples have been reported of the synthesis of aldonic acids by carbon-carbon bond-forming reactions. 2,3 4,5-Di-0-isopropylidene-D-arabinose (3) with methyl acetoacetate gave the Knoevenagel product (4), which is a branched-chain, unsaturated heptonic acid derivative. This rearranged on treatment with trifluoroacetic acid to afford the spiro-product (5) (Scheme 1). This same compound was obtainable from the 2,5-anhydroaldose derivative (6) by similar treatment. The synthesis of destomic acid, 6-amino-6-deoxy-L- /ycew-... 

Addition of the Grignard reagent PhMe2SiCH2MgCl to the D-ga/ncto-aldehyde 34, followed by oxidative desilyladon, were key steps in a synthesis of destomic acid (35). ... 

Chain Extension. - Aldolase-catalysed aldol condensation reactions used in the synthesis of sialic acids and aza-sugars have been reviewed (38 refs.). Addition of 2-thiazolyl reagents to the nitrone 2, available from the D-galacto-dialdose 1, featured in syntheses of destomic acid 3 and... 

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