Bromodeoxy aldonolactones

The use of bromodeoxy lactones as chiral building blocks for the stereoselective preparation of natural compounds was also explored. Thus, both (5)-and (J )-carnitine, (S)- and (J )-4-amino-3-hydroxybutanoic acid (GABOB), compounds of high relevance for the central nervous system, as well as musc-aridine and 6-deoxyascorbic acid, were prepared by simple transformations of the bromodeoxy aldonolactones. 

From Bromodeoxy/Tosyloxy Aldonolactones to Other Lactone Synthons... 

Tetrahydrofurans from Bromodeoxy/Tosyloxy Substituted Aldonolactones... 

When the bromodeoxy lactones were boiled in water tetrahydrofurans were formed, whereas catalytic hydrogenation caused deoxygenation at C-2 and/or at the primary position, while the acetylated aldonolactones could also be reduced to 3-deoxylactones after elimination and stereospecific reduction. Substitution by azide introduced nitrogen functions at C-2 or at both bromo-substituted carbons, and these compounds could be converted into the corresponding amino acids. The new molecules could furthermore be reduced to the corresponding aldoses or alditols. 

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