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US 6,545,184 B1Granted
Practical, cost-effective synthesis of COQ10
AssigneeThe Regents of the University of California
InventorBruce H. Lipshutz
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Abstract
The present invention provides a convergent method for the synthesis of ubiquinones and ubiquinone analogues. Also provided are precursors of ubiquinones and their analogues that are useful in the methods of the invention.
Claims42
A compound according to Formula I:
- wherein,
- R1, R2 and R3 are independently selected C1-C6 alkyl groups;
- R4 is a sulfonate;
- R5 is a member selected from the group consisting of branched, unsaturated alkyl, —C(O)H, and —CH2Y, in which Y is OR6, SR6, NR6R7, or a leaving group;
- R6 and R7 are members independently selected from H and branched, unsaturated alkyl.
2 more elements
A method for preparing a compound according to Formula IV:
- wherein,
- R1, R2 and R3 are members independently selected from the group consisting of C1-C6 alkyl groups;
- n is a member selected from group consisting of the integers from 0 to 13, said method comprising:
- (a) contacting a compound according to Formula V:
- wherein,
- Y is a leaving group;
- R4 is a protecting group, with a compound according to Formula VI:
- wherein,
- L is an organometallic ligand;
- M is a metal;
- p is a member selected from the group consisting of the integers from 1 to 5, wherein each of said p organometallic ligands is independently selected;
- n is a member selected from the group consisting of the integers from 0 to 13,
- in the presence of a catalyst effective at catalyzing coupling between a benzylic carbon atom according to Formula V and an organometallic species according to Formula VI, thereby forming a compound according to Formula VII:
- (b) removing R4, thereby producing a compound according to Formula VIII:
- (c) contacting the compound according to Formula VIII with an oxidant, thereby producing a compound according to Formula IV.
12 more elements
Dependencies are inferred from the claim text.