48 dl-Phyllodulcinの全合成

概要

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D-Phyllodulcin, a sweetening agent, was first isolated and characterized as dihydroisocoumarin by Asahina and Asano and its absolute configuration determined by Arakawa. We have developed a practical route to DL-8-desoxyphyllodulcin and successfully applied it to the total synthesis of DL-phyllodulcin. First, the condensation of diesters of homophthalic acid with aromatic aldehydes with DBU followed by cyclization, has provided a convenient route to 3-aryldihydro-isocoumarin derivatives. This condensation gave excellent yields of the cinnamic esters which were subsequently cyclized by hydrogen bromide in chloroform or acetic acid to the dihidroisocoumarin. And then, DL-8-desoxy-phyllodulcin and DL-phyllodulcin was obtained by heating an aqueous solution of dihydroisocoumarin derivatives at correspond temperature with sulfuric acid or AlBr_3 as catalyst in autoclave.
1973-10-01