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... 

An elegant total synthesis of the semiprotected form of lincosamine was realized by Marshall and Beaudoin [116]. An aldehyde derived from destomic acid (6-amino-6-deoxy-L-g/yc ro-D-ga/acto-heptonic acid) was derived in a similar way from a L-serinal derivative via hetero Diels-Alder addition to 1-ethoxy-3-[(trimethylsilyl)oxy]-4-benzyloxy-1,3-butadiene [142]. A similar method was applied to the preparation of a semiprotected form of anhydrogalantinic acid, a component of the antibiotic galantin I [142]. 

Marshall, J A, Beaudoin, S, Stereoselective synthesis of differentially protected derivatives of the higher amino sugars destomic acid and hncosamine from serine and threonine, J. Org. Chem., 61, 581-586, 1996. 

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). ... 

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