179260-96-9Relevant articles and documents
Total syntheses of (±)-musellarins A-C
Li, Zhilong,Leung, Tsz-Fai,Tong, Rongbiao
, p. 10990 - 10993 (2014)
The first, diastereoselective total syntheses of musellarins A-C were achieved concisely with 7.8-9.8% yields in 15-16 steps. The key synthetic features include (i) an Achmatowicz rearrangement, Kishi reduction, and Friedel-Crafts cyclization to construct
Reactive group-embedded affinity labeling reagent for efficient intracellular protein labeling
Takaoka, Yousuke,Nukadzuka, Yuuki,Ueda, Minoru
, p. 2888 - 2894 (2017)
Affinity labeling of a target protein is a powerful method for chemical biology studies. However, it is still difficult to label intracellular proteins efficiently in living cells. We propose the novel design strategy of a reactive group-embedded affinity
Asymmetric synthesis of fortucine and reassignment of its absolute configuration
Beaulieu, Marc-Andre,Ottenwaelder, Xavier,Canesi, Sylvain
supporting information, p. 7581 - 7584 (2014/07/07)
A convergent and enantioselective synthesis of fortucine was achieved from the starting materials tyrosine methyl ester and 3-hydroxy-4- methoxybenzaldehyde. The synthesis is based on two key steps mediated by a hypervalent iodine reagent. This work has enabled us to reassign the absolute configuration of the natural product reported in the literature. A multi-tool for total synthesis: A convergent and enantioselective synthesis of fortucine was achieved from the starting materials tyrosine methyl ester and 3-hydroxy-4-methoxybenzaldehyde. The synthesis is based on two key steps mediated by a 'multi-tool' hypervalent iodine reagent (see scheme).
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].
