103791-54-4Relevant academic research and scientific papers
Non-natural Acetogenin Analogues as Potent Trypanosoma brucei Inhibitors
Florence, Gordon J.,Fraser, Andrew L.,Gould, Eoin R.,King, Elizabeth F. B.,Menzies, Stefanie K.,Morris, Joanne C.,Tulloch, Lindsay B.,Smith, Terry K.
, p. 2548 - 2556 (2014)
Neglected tropical diseases remain a serious global health concern. Here, a series of novel bis-tetrahydropyran 1,4-triazole analogues based on the framework of chamuvarinin, a polyketide natural product isolated from the annonaceae plant species are deta
Synthesis of Vicinal Dichlorides via Activation of Aliphatic Terminal Epoxides with Triphosgene and Pyridine
Cleveland, Alexander H.,Fronczek, Frank R.,Kartika, Rendy
, p. 3367 - 3377 (2018/03/26)
Herein we report a novel synthetic reaction to convert unactivated terminal aliphatic epoxide to alkyl vicinal dichloride based on triphosgene-pyridine activation. Our methodology is operationally simple and readily tolerated by a broad of scope of substrates as well as protecting groups. Furthermore, these mild conditions generally yield clean reaction mixtures that are free of byproducts upon aqueous workup.
Non-natural Acetogenin Analogues as Potent Trypanosoma brucei Inhibitors
Florence, Gordon J.,Fraser, Andrew L.,Gould, Eoin R.,King, Elizabeth F. B.,Menzies, Stefanie K.,Morris, Joanne C.,Tulloch, Lindsay B.,Smith, Terry K.
supporting information, p. 2548 - 2556 (2015/08/24)
Neglected tropical diseases remain a serious global health concern. Here, a series of novel bis-tetrahydropyran 1,4-triazole analogues based on the framework of chamuvarinin, a polyketide natural product isolated from the annonaceae plant species are deta
Study of the total synthesis of (-)-exiguolide
Cook, Cyril,Liron, Frederic,Guinchard, Xavier,Roulland, Emmanuel
scheme or table, p. 6728 - 6742 (2012/09/21)
In this article, we disclose the various routes and strategies we had to explore before finally achieving the total synthesis of (-)-exiguolide ((-)-1). Two first types of approaches were set, both relying on the Trost's domino ene-yne coupling/oxa-Michael reaction that we choose for its ability to control the geometry of the methylacrylate-bearing tetrahydropyrane ring B. In our first approach, we expected to assemble the two main fragments (C14-C21 and C1-C13) by creating the C13-C14 bond through a palladium(0)-catalyzed cross-coupling, but this step failed, unfortunately. In the second approach, which was more linear, we created the C16-C17 bond through condensation of a lithium acetylide on a Weinreb amide, and we assembled the C1-C5 and C6-C21 subunits through Trost's domino ene-yne coupling/oxa-Michael reaction. These two approaches served us to design an ameliorated third strategy, which finally led to the total synthesis of (-)-exiguolide.
Total synthesis of (-)-exiguolide
Cook, Cyril,Guinchara, Xavier,Liron, Frederic,Roulland, Emmanuel
, p. 744 - 747 (2011/03/17)
The first total synthesis of the naturally occurring enantiomer of exiguolide ((-)-1) has been completed. This very convergent synthesis features the following as main steps: (I) a Trost's ruthenium-catalyzed ene-yne cross-coupling reaction (this complex transformation allows the challenging control of the C5-C28 double bond geometry along with the stereoselective construction of the tetrahydropyran ring A) and (II) a very efficient one-pot, two-step stereoselective conjugated allyllc alcohol substitution that allowed the control of the C15 stereogenic center.
"Cassette" in situ enzymatic screening identifies complementary chiral scaffolds for hydrolytic kinetic resolution across a range of epoxides
Dey, Sangeeta,Powell, Douglas R.,Hu, Chunhua,Berkowitz, David B.
, p. 7010 - 7014 (2008/09/17)
(Figure Presented) Put the cassette in: An in situ enzymatic screen can give real-time estimates of the sense and magnitude of enantioselectivity across more than one substrate. Screening identified CoIII-salen catalysts with β-pinene- and α-naphthylalanine-derived chiral scaffolds with broad, yet complementary, substrate specificities. ADH = alcohol dehydrogenase, HL = horse liver, LK = Lactobacillus kefir, salen = (salicylidene) ethylenediamine.
Novel oxepane formation by TiCl4-catalyzed nucleophilic cleavage of 1- alkoxymethyl-6,8-dioxabicyclo[3.2.1]octanes
Fujiwara, Kenshu,Amano, Arika,Tokiwano, Tetsuo,Murai, Akio
, p. 1065 - 1080 (2007/10/03)
Introduction of an alkoxymethyl group at the C1 position in the 6,8- dioxabicyclo[3.2.1]octane system enabled novel formation of oxepane compounds in TiCl-4-catalyzed acetal cleavage reactions. (C) 2000 Elsevier Science Ltd.
DILITHIUM TETRACHLOROCUPRATE. A REAGENT FOR REGIOSELECTIVE CLEAVAGE OF EPOXIDE TO CHLOROHYDRINS.
Ciaccio, James A.,Addess, Kenneth J.,Bell, Thomas W.
, p. 3697 - 3700 (2007/10/02)
The title compound reacts with epoxides to selectively afford the vicinal chlorohydrin resulting from attack by chloride at the less substituted carbon atom.
