Synthesis of l-muscone by asymmetric methylation via enol esters.
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.
Matsuda
Hiroyuki
H
Takasago International Corporation, Central Research Laboratory, 1-4-11 Nishi-yawata, Hiratsuka city, Kanagawa 254-0073, Japan. hiroyuki_matsuda@takasago.com
Tanaka
Shigeru
S
Yamamoto
Kenichi
K
Ishida
Kenya
K
D003516:Cycloparaffins / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D008745:Methylation; D015394:Molecular Structure; D010476:Perfume / Q000138:chemical synthesis* / Q000737:chemistry
D003516:Cycloparaffins; D004952:Esters; D010476:Perfume; C031021:muscone