LIPASE-CATALYZED SITE-SELECTIVE DEACETYLATION OF STERICALLY HINDERED NAPHTHOHYDROQUINONE DIACETATE AND ITS APPLICATION TO THE SYNTHESIS OF A HETEROCYCLIC NATURAL PRODUCT

摘要

Lipase-catalyzed site-selective deacetylation of 2,5-dimethylnaphthalene-1,4-diol diacetate was examined. With Candida antarctica lipase B, the suppressing effect of a methyl substituent at the peri-position of the alpha-naphthyl ester over that at the ortho-position was significant. This site-selectivity was in contrast to that of chemical hydrolysis reported to date. From the resulting monoacetate, mansonone F, a physiologically active heterocyclic orthoquinone, was synthesized in 38% yield in as few as three steps.