Abstract
It is highly important to find a novel chiral building unit for the synthesis of enantiopure natural products of biological interest and also for developing novel asymmetric reactions.L-Quebrachitol (1L- (-) -2-O-methyl-chiro-inositol) is a naturally occurring optically active cyclitol obtained from an exudate of the rubber tree. By developing novel method for the selective demethylation of methyl ether in the presence of cyclohexylidene acetal in L-quebrachitol moieties, total syntheses of myo-inositol 1-phosphate, (+) -conduritol B, and cyclophellitol were achieved.It was found that chiral cyclitols derived from L-quebrachitol were excellent chiral auxiliaries. For instance, diastereoselective reduction and addition to α-keto ester attached to chiral cyclitol derivatives took place highly stereoselectively. Diels-Alder reactions and [3+2] cycloaddition of nitrile oxide to acryloyl ester derived from the chiral cyclitol also proceeded with high diastereoselectivity.
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