Chiral Aldehydes as Dienophiles Synthesis of Long-Chain Sugars

2 Chiral Aldehydes as Dienophiles Synthesis of Long-Chain Sugars 

274 was transformed into the 6-amino-6,8-dideoxy-L-r/tr 9-L-ga/acto-octopyranose derivative 

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]. 

SCHEME 13.78 Danishefsky s synthesis of lincosamine and Jurczak s synthesis of a lincosamine isomer. 

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