California Institute of Technology

Umicore Ag & Co Kg

Tonia S Ahmed

Robert H Grubbs

T Patrick Montgomery

Brian M Stoltz

Jiaming Li

Richard L Pederson

Adam M Johns

Choon Woo Lee

Chen Xu

Pablo E Guzman

Xu Chen

T Patric Montgomery

This invention relates generally to the synthesis of Δ-Prostaglandin J product using stereoretentive ruthenium olefin metathesis catalysts supported by dithiolate ligands. Δ-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).

Total synthesis of prostaglandin J natural products by stereoretentive metathesis

A highly efficient, Z-selective ring-closing metathesis system for the formation of macrocycles using a stereoretentive, ruthenium-based catalyst supported by a dithiolate ligand is reported. This catalyst is demonstrated to be remarkably active as observed in initiation experiments showing complete catalyst initiation at &#x2212;20&#xb0; C. within 10 min. Using easily accessible diene starting materials bearing a Z-olefin moiety, macrocyclization reactions generated products with significantly higher Z-selectivity in appreciably shorter reaction times, in higher yield, and with much lower catalyst loadings than in previously reported systems. Macrocyclic lactones ranging in size from twelve-membered to seventeen-membered rings are synthesized in moderate to high yields (68-79% yield) with excellent Z-selectivity (95%-99% Z).

Highly efficient synthesis of Z-macrocycles using stereoretentive, ruthenium-based metathesis catalysts

This invention relates generally to the synthesis of E-macrocycles using stereoretentive ruthenium olefin metathesis catalysts supported by dithioiate ligands. Macrocycles were generated with excellent selectivity (&#x3e;99% E) and in moderate to high/good yields (47% to 80% yield; 58% to 80% yield) from diene starting materials bearing two E-olefins or bearing one E-olefin and one terminal olefin, A variety of rings were constructed, ranging from 12- to 18-membered macrocycles, including the antibiotic recifeiolide. The invention has utility in the fields of organometallics and organic synthesis.

Using stereoretention for the stereoselective formation of e-macrocycles with Ru-based olefin metathesis catalysts

Highly efficient synthesis of z-macrocycles using stereoretentive, ruthenium-based metathesis catalysts

The present disclosure is directed to methods of preparing prostaglandin J natural products by stereoretentive metatheses reactions and intermediates used in the synthesis of these natural products, including the use of intermediates of Formula (I-A), where Ris defined in the specification 

Total synthesis of prostaglandin J natural products and their intermediates

This invention relates generally to metathesis catalysts and the use of such catalysts in the metathesis of olefins and olefin compounds, more particularly, in the use of such catalysts in Z and E selective olefin metathesis reactions. The invention has utility in the fields of organometallics and organic synthesis.

Olefin metathesis catalysts

This invention relates generally to olefin metathesis catalyst compounds, to the preparation of such compounds, and the use of such catalysts in the metathesis of olefins and olefin compounds, more particularly, in the use of such catalysts in (E)-selective olefin metathesis reactions. The invention has utility in the fields of catalysis, organic synthesis, polymer chemistry, and industrial and fine chemicals chemistry.

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Pasadena, CA, United States of America

Tonia S Ahmed