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Synthesis of l ‐Muscone by Asymmetric Methylation via Enol Esters
Author(s) -
Matsuda Hiroyuki,
Tanaka Shigeru,
Yamamoto Kenichi,
Ishida Kenya
Publication year - 2008
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200890082
Subject(s) - enol , chemistry , methylation , enone , resolution (logic) , organic chemistry , stereochemistry , biochemistry , catalysis , artificial intelligence , computer science , gene
An effective synthetic route of l ‐muscone ( 1 ) by asymmetric methylation, followed by enolate‐trapping to generate enol esters as intermediates, was described. Interestingly, the enol esters can be used as substrates for enzymatic optical resolution to improve optical purity. Additionally, several excellent new chiral ligands were discovered for asymmetric methylation of ( E )‐cyclopentadec‐2‐enone to produce l ‐muscone with high optical purity.