专利号:US-11866398-B2 优先权日:2018-05-15 标 题:Total synthesis of prostaglandin J natural products by stereoretentive metathesis 发明人:LI JIAMING; CHEN XU; AHMED TONIA S; STOLTZ BRIAN M; GRUBBS ROBERT H 权利人:CALIFORNIA INST OF TECHN 摘要: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).
专利号:WO-2025217205-A1 优先权日:2024-04-08 标 题:Synthesis of (-)-trans-δ9-tetrahydrocannabivarin (δ9-thcv) and analogs thereof 发明人:HAGHDOOST MEHDI; ROBERTS MATTHEW; THOMAS BRIAN; DICKINSON LUKE; NIKITIN EDWARD 权利人:NALU BIO INC 摘要:A method is provided for the synthesis of (-)-trans-Δ9-tetrahydrocannabivarin (Δ9-THCV) and analogs thereof such that in the reaction product, the molar ratio of the Δ9 isomer to incidentally formed Δ8 isomers is greater than 4:1. Synthesis is carried out by combining a selected cannabinoid reactant, e.g., cannabidivarin (CBDV) or an analog thereof, with an acid in a solvent for the cannabinoid reactant, wherein the acid comprises (i) a Lewis acid having an acid softness index value in the range of -10 ΔG0 f, M n+ to ‑150 ΔG0 f, M n+, (ii) a Brønsted acid having a pKa in the range of -4.0 to +4.0, or (iii) a combination of (i) and (ii), under reaction conditions comprising a reaction temperature in the range of ‑0 °C to 25 °C and a reaction time in the range of 1 hour to 24 hours. The reaction is thereafter quenched with base and the solvent removed, wherein the crude reaction product so provided may be purified, e.g., chromatographically purified. Also provided is a method for synthesizing Δ9-THCV that further includes synthesis of the cannabinoid reactant. The invention additionally provides novel cannabinoid compositions that may be synthesized using the aforementioned methodology.
专利号:US-12264143-B2 优先权日:2020-12-17 标 题:Synthesis of cannabinoids and cannabinoid precursors, and related compounds, formulations, and methods of use 发明人:SAMMIS GLENN M; ROGGEN MARKUS 权利人:NALU BIO INC 摘要:Methods are provided for the synthesis of cannabinoids, including cannabidiol (CBD), cannabinol (CBN), cannabichromene (CBC), cannabidiolic acid (CBDA), cannabigerol (CBG), cannabigerolic acid (CBGA), cannabidivarin (CBDV), cannabidibutol (CBD-C4), dihydrocannabidiol (DCBD), tetrahydrocannabivarin (THCV), analogs thereof, and precursors to the foregoing. One method employs phloroglucinol or a phloroglucinol analog as a starting material. The syntheses are stereospecific, efficient, selective, and cost-effective, with little or no potential for generation of THC ((−)-trans-Δ9-tetrahydro-cannabinol) or any other psychoactive side product. Telescoped syntheses are also provided, as are new cannabinoids, pharmaceutical formulations, and methods of use.
专利号:US-11407726-B2 优先权日:2017-12-06 标 题:Using stereoretention for the stereoselective formation of e-macrocycles with Ru-based olefin metathesis catalysts 发明人:AHMED TONIA S; MONTGOMERY T PATRICK; GRUBBS ROBERT H 权利人:CALIFORNIA INST OF TECHN 摘要: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 (>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.
专利号:US-11794179-B2 优先权日:2016-08-24 标 题 :Synthesis and characterization of metathesis catalysts 发明人:JOHNS ADAM M 权利人:UMICORE AG & CO KG 摘要:This invention relates generally to olefin metathesis catalysts, to the preparation of such compounds, compositions comprising such compounds, methods of using such compounds, and the use of such compounds in the metathesis of olefins and in the synthesis of related olefin metathesis catalysts. The invention has utility in the fields of catalysis, organic synthesis, polymer chemistry, and in industrial applications such as oil and gas, fine chemicals and pharmaceuticals.
专利号:US-11773118-B2 优先权日:2019-02-21 标 题:Methods of making high enantioselective secondary alcohols 发明人:YU CHENG-DER TONY; HSIEH YIH-HUANG; LIN SHU-YI; CHAO CHIN-SHENG; HSIEH YIN-CHENG; LAI MING-TAIN 权利人:OBI PHARMA INC 摘要:A new process to synthesis of compound OBI-3424 R-form and S-form products is provided. The “R-formâ€? compound OBI-3423 was first synthesized with 48% overall yield from compound OBI-3424-5 by installation of the labile phosphate motif at later stage. The stereo chemistry is established by 5 steps chemo-enzyme combination synthesis to afford 99% optical purity. After then, the “S-formâ€? compound OBI-3424 is prepared with improving overall yield of 54% from compound OBI-3424-5. The stereo chemistry is established by 4 steps combination of chemo-enzyme synthesis with excellent optical purity of 99%.
参考文献:10.1038/srep20473 摘要:Fujikawa A, Nagahira A, Sugawara H, Ishii K, Imajo S, Matsumoto M, Kuboyama K, Suzuki R, Tanga N, Noda M, Uchiyama S, Tomoo T, Ogata A, Masumura M, Noda M. Small-molecule inhibition of PTPRZ reduces tumor growth in a rat model of glioblastoma. Scientific Reports. 2016 Feb 09;6(1):20473. doi: 10.1038/srep20473.