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• W2030089213 endingPage "214" @default.
• W2030089213 startingPage "197" @default.
• W2030089213 abstract "Starting from inexpensive (E)-β-farnesene (1), an eight-step enantioselective synthesis of the olfactively precious Ambrox® ((−)-2a) has been performed. The crucial step is the catalytic asymmetric isomerization of (2E,6E)-N,N-diethylfarnesylamine (3) to the corresponding enamine (−)-(R,E)-4a, applying Takasago's well-known industrial methodology. The resulting dihydrofarnesal ((+)-(R)-5) (90% yield, 96% ee), obtained after in situ hydrolysis (AcOH, H2O), was then cyclized under catalytic SnCl4 conditions, via its corresponding unreported enol acetate (−)-(R)-4b, to afford trans-decalenic aldehyde (+)-6a. Subsequent transformations furnished bicyclic ketone (−)-8a and unsaturated nitrile (+)-11, both reported as intermediates to access to (−)-2a." @default.
• W2030089213 created "2016-06-24" @default.
• W2030089213 creator A5005552971 @default.
• W2030089213 date "2014-02-01" @default.
• W2030089213 modified "2023-10-17" @default.
• W2030089213 title "Enantioselective Access to (−)-<i>Ambrox</i>^®Starting from<i>β</i>-Farnesene" @default.
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