A Polyhydroxylated Cyclopentene: A Useful Synthon toward the Synthesis of Carbocyclic D-Fructofuranoid
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چکیده
Fructose 2,6-bisphosphate (1) is formed by phosphorylation of fructose-6-phosphate, a key substrate in the glycolysis pathway, in a reaction catalyzed by phosphofructokinase-2 (PFK-2) [1]. Fructose-2,6-bisphosphate is a powerful allosteric regulator of glycolysis via its potent stimulatory effect on phosphofructokinase-1 activity and its in hibitory effect on fructose-1,6-bisphosphatase. The recent identification of an inducible isoform of PFK-2 that is specifically induced by inflammation stimuli or oncogenic transformation has suggested that fructose analogs might serve as useful phar macophores for inhibiting cell activation and can cer cell growth [2, 3]. Unlike phosphorylated fruc tose, carbocyclic D-fructofuranoside (2) (Fig. 1) can not be metabolized and therefore can be shut tled repeatedly through cycles of kinase and phos phatase activity. Wilcox and Guadino [4] have shown the first and only synthetic approach to carbocyclic D-fructofuranoside (3) (Scheme 1). The overall synthesis in volved 12 steps. Cyclopentane ring closure was accomplished utilizing a free-radical mediated
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