179260-99-2Relevant academic research and scientific papers
Highly enantioselective synthesis of natural phyllodulcin
Ramacciotti, Alessio,Fiaschi, Rita,Napolitano, Elio
, p. 5371 - 5374 (2007/10/03)
(S)-[4-Methoxy-3-[(triisopropylsilyl)oxy]phenyl)oxirane (prepared from isovanillin by consecutive silylation, olefination, Sharpless asymmetric cis-dihydroxylation, and dehydration) reacted with [3-(methoxymethoxy)phenyl]lithium (prepared from 3-bromophenol by consecutive methoxymethylation and bromine-lithium exchange) to yield (R)-1-[4-methoxy-3-[(triisopropylsilyl)oxy]phenyl)2-[3-(methoxymethoxy )phenyl]ethanol. The last compound underwent selective hydrogen-metal exchange with excess of butyllithium affording (after carbonation, lactonization, and deprotection of phenolic groups) the title compound [(R)-3,4-dihydro-8-hydroxy-3-(4-methoxy-3-hydroxyphenyl)isocoumarin].
