Terpenoid derivatives obtained from terpenoids steming from renewable sources
AssigneeEcole Nationale Superieure De Chimie De Rennes
InventorsMarc Mauduit, Frédéric Caijo, Christophe Crévisy
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Abstract
The present invention relates to a process for preparing a terpenoid derivative, the process comprising a metathesis of an olefin and a terpenoid, and to terpenoid derivatives prepared with said process.
Claims15
A process for obtaining a terpenoid derivative, the process comprising:
- a metathesis of an olefin and a terpenoid, wherein the terpenoid has the following general formula:
- wherein R1 is
- n is 0 and R2 is
- or
- R1 is
- n is 0 and R2 is
- or
- R1 is
- n is 1 and R2 is —C(H)═O or —C(H2)—OAc, and
- wherein R3 and R4 are the same or different and are each independently hydrogen or alkyl, and
- wherein the olefin has the following general formula:
- wherein R7, R8, R13 and R14 are the same or different and are each independently hydrogen, alkyl, halo, haloalkyl, alkenyl, alkynyl, cycloalkyl, aryl, arakyl, alkoxy, carbonyl, carboxyl, hydroxyl, amide, sulfonamide, or amine;
- wherein when n=1, R7 and R8 are not both —CH3;
- and
- wherein when n=0, R7 and R8 together are different from R3 and R4 together.
A terpenoid derivative having the following general formula:
- wherein R5 is
- n is 0 and R6 is
- or
- R5 is
- n is 0 and R6 is
- or
- R5 is
- n is 0 and R6 is
- or
- R5 is
- n is 1 and R6 is —C(H)═O or —C(H2)—OAc,
- wherein R3 and R4 are the same or different and are each independently hydrogen or alkyl,
- wherein R7 and R8 are the same or different and are each independently hydrogen, alkyl, halo, haloalkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, alkoxy, carbonyl, carboxyl, hydroxyl, amide, sulfonamide, or amine, and
- wherein when R5 is
- R7 and R8 are not both hydrogen, and
- wherein when R5 is
- R7 and R8 are not both —CH3.
A terpenoid derivative having the following general formula:
- wherein R9 is
- and R10 is
- or
- R9 is
- and R10 is
- wherein R7, R8, R11 and R12 are the same or different and are each independently hydrogen, alkyl, halo, haloalkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, alkoxy, carbonyl, carboxyl, hydroxyl, amide, sulfonamide, or amine,
- wherein when R9 is
- and when R11 and R12 are both hydrogen, R7 and R8 are not both —CH3, and
- wherein when R9 is
- and when R7 and R8 are both hydrogen, R11 and R12 are not both —CH3.
Use of a ruthenium Hoveyda type catalyst for the preparation of a terpenoid derivative by the catalyzed olefin cross-metathesis of a terpenoid with an olefin, the catalyst having the general formula:
- wherein and R is CF3, CO2Et, OiBu, C6F5 or C15H31, and
- wherein L is
- or having the general formula:
- or having the general formula
- wherein SIMes is
Dependencies are inferred from the claim text.