68224-83-9

Upstream product

• 106-25-2 Nerol 
• 79194-57-3 3-(chloromethyl)-2-methyl-2-(4-methylpent-3-en-1-yl)oxirane 
• 50727-94-1 (2R,3R)-3-methyl-3-(4-methyl-3-pentenyl)oxiranemethanol 
• 106-24-1 Geraniol 
• 62777-72-4 (2R,3S)-2,3-epoxynerol 
• 168254-29-3 (2S,3S)-3-Chloromethyl-2-methyl-2-(4-methyl-pent-3-enyl)-oxirane 
• 79194-57-3 (2S,3S)-3-Chloromethyl-2-methyl-2-(4-methyl-pent-3-enyl)-oxirane 
• 79194-57-3 (2S,3R)-3-(chloromethyl)-2-methyl-2-(4-methylpent-3-en-1-yl)oxirane 
• 624-15-7 geraniol 
• 82188-73-6 (2S,3S)-2,3-epoxygeraniol 

Relevant academic research and scientific papers

Bridgehead Modifications of Englerin A Reduce TRPC4 Activity and Intravenous Toxicity but not Cell Growth Inhibition

Modifications at the bridgehead position of englerin A were made to explore the effects of variation at this site on the molecule for biological activity, as judged by the NCI 60 screen, in which englerin A is highly potent and selective for renal cancer cells. Replacement of the isopropyl group by other, larger substituents yielded compounds which displayed excellent selectivity and potency comparable to the natural product. Selected compounds were also evaluated for their effect on the ion channel TRPC4 as well as for intravenous toxicity in mice, and these had lower potency in both assays compared to englerin A.

ENGLERIN DERIVATIVES FOR TREATMENT OF CANCER

Disclosed is a compound of formula (I) in which a, R1- R5 and X1 are as described herein. Also disclosed are a pharmaceutical composition containing the compound and a method of using the compound for treating cancer, such as renal cancer.

α,β-Unsaturated Gold(I) Carbenes by Tandem Cyclization and 1,5-Alkoxy Migration of 1,6-Enynes: Mechanisms and Applications

1,6-Enynes bearing OR groups at the propargyl position generate α,β-unsaturated gold(I)-carbenes/ gold(I) stabilized allyl cations that can be trapped by alkenes to form cyclopropanes or 1,3-diketones to give products of α-alkylation. The best migrating group is p-nitrophenyl ether, which leads to the corresponding products without racemization. Thus, an improved formal synthesis of (+)-schisanwilsonene A has been accomplished. The different competitive reaction pathways have been delineated computationally.

Synthesis and Biological Evaluation of New (-)-Englerin Analogues

We report the synthesis and biological evaluation of a series of (-)-englerin A analogues obtained along our previously reported synthetic route based on a stereoselective gold(I) cycloaddition process. This synthetic route is a convenient platform to access analogues with broad structural diversity and has led us to the discovery of unprecedented and easier-to-synthesize derivatives with an unsaturation in the cyclopentyl ring between C4 and C5. We also introduce novel analogues in which the original isopropyl motif has been substituted with cyclohexyl, phenyl, and cyclopropyl moieties. The high selectivity and growth-inhibitory activity shown by these new derivatives in renal cancer cell lines opens new ways toward the final goal of finding effective drugs for the treatment of renal cell carcinoma (RCC).

EPOXYAZULENE DERIVATIVES USEFUL FOR TREATING CANCER AND DIABETES

Disclosed is a compound of formula (I) in which R1-R5 and X1 are as described herein. Also provided are methods of using a compound of formula (I), including a method of treating cancer and a method of treating diabetes.

Construction of 1,5-enynes by stereospecific Pd-catalyzed allyl-propargyl cross-couplings

The palladium-catalyzed cross-coupling of chiral propargyl acetates and allyl boronates delivers chiral 1,5-enynes with excellent levels of chirality transfer and can be applied across a broad range of substrates.

Enantioselective synthesis of (-)-englerins A and B

Chemical Equation Present. All that glitters is gold: The total synthesis of the natural enantiomers of englerins A and B has been completed using a goldcatalyzed stereoselective domino alkyne/alkene/carbonyl cyclization of an enyne with an unprotected alcohol group at a stereogenic allylic position (see scheme; TES = triethylsilyl).

A short and efficient synthetic strategy for the total syntheses of (S)-(+)- and (R)-(-)-Plakolide A

Concise and efficient total syntheses of anticancer agents (S)-(+)-Plakolide A and (R)-(-)-Plakolide A were accomplished in eight steps and an overall yield of 39 % starting from geraniol. The key steps in our strategy are Sharpless asymmetric epoxidation, double elimination, and Stille coupling reactions. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Stereoselective synthesis of β-ketoesters from prop-2-yn-1-ols

The activation of allylic prop-2-yn-1-ols by the [Ru(μ-O2CH)(CO)2(PPh3)]2 catalyst in the presence of carboxylic acids leads to unsaturated β-ketoesters in one step. The utilization of optically active prop-2-yn-1-ols provides a new stereoselective access to optically active β-ketoesters with retention of configuration at the propargylic carbon.

Base induced opening of 2,3-epoxychlorides: An efficient preparation of trans-chlorovlnyl alcohols

A highly efficient protocol for the sythesis of of chiral trans-1-chlorvinyl alcohols (2) from chiral 2,3-epoxychloride is described by using stoicheiometric amount of LiNH2 or LDA.