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US 11,866,398 B2Granted
Total synthesis of prostaglandin J natural products by stereoretentive metathesis
AssigneeCalifornia Institute of Technology
InventorsJiaming Li, Xu Chen, Tonia S. Ahmed, Brian M. Stoltz, Robert H. Grubbs
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Abstract
This invention relates generally to the synthesis of Δ12-Prostaglandin J product using stereoretentive ruthenium olefin metathesis catalysts supported by dithiolate ligands. Δ12-Prostaglandin J products were generated with excellent selectivity (>99% Z) and in moderate to high/good yields (47% to 80% yield; 58% to 80% yield).
Claims10
A method for producing at least one Δ12-Prostaglandin J product represented by Formula (IV),
- wherein:
- Rz is selected from
- and wherein at least one carbon-carbon double bond has a Z/E-selectivity of 95/5, or 96/4, or 97/3, or 98/2, or 99/1, or >99/<1;
- comprising, submitting an alcohol product of Formula (III)
- to oxidation conditions;
- wherein the alcohol product of Formula (III) is formed during a cross-metathesis reaction between a substrate represented by Formula (II)
- and cis-5-octen-1-ol in the presence of a ruthenium olefin metathesis catalyst;
- and wherein Rv is selected from
5 more elements
Dependencies are inferred from the claim text.