HIGHLY ENANTIOSELECTIVE SYNTHESIS OF NATURAL PHYLLODULCIN

4-Methoxy-3-[(triisopropylsilyl)oxy]phenyl)oxirane (prepared from isov anillin by consecutive silylation, olefination, Sharpless asymmetric c is-dihydroxylation, and dehydration) reacted with [3-(methoxymethoxy)p henyl]lithium (prepared from 3-bromophenol by consecutive methoxymethy lation and bromine - lithium exchange) to yield opylsilyl)oxy]phenyl)- 2-[3-(methoxymethoxy)phenyl] ethanol. The last compound underwent sele ctive hydrogen-metal exchange with excess of butyllithium affording (a fter carbonation, lactonization, and deprotection of phenolic groups) the title compound ydroxy-3-(4-methoxy-3-hydroxyphenyl)-isocoumarin].