7214-52-0Relevant academic research and scientific papers
SYNTHESIS OF HALICHONDRINS
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Paragraph 00752, (2019/01/21)
The present invention provides methods for the synthesis of ketones involving a Ni/Zr-mediated coupling reaction. The Ni/Zr-mediated ketolization reactions can be used in the synthesis of halichondrins (e.g., halichondrin A, B, C; homohalichondrin A, B, C; norhalichondnn A, B, C), and analogs thereof. Therefore, the present invention also provides synthetic methods useful for the synthesis of halichondrins, and analogs thereof. Also provided herein are compounds (i.e., intermediates) useful in the synthesis of halichondrins, and analogs thereof. In particular, the present invention provides methods and compounds useful in the synthesis of compound of Formula (H3-A)
Enantioselective synthesis of BE ring analogues of methyllycaconitine
Dickson, Emma,Pilkington, Lisa I.,Brimble, Margaret A.,Barker, David
, p. 400 - 414 (2015/12/31)
The enantioselective synthesis of decahydroquinolines mimicking the BE rings of methyllycaconitine (MLA) is reported. The analogues were synthesised via a one-pot cyclisation using ethyl α-(bromomethyl)acrylate, (R)-1-phenylethanamine and cyclohexanone to
A Scalable Synthesis of (R,R)-2,6-Dimethyldihydro-2H-pyran-4(3H)-one
Young, Ian S.,Haley, Matthew W.,Tam, Annie,Tymonko, Steven A.,Xu, Zhongmin,Hanson, Ronald L.,Goswami, Animesh
, p. 1360 - 1368 (2015/11/02)
A scalable synthesis of (R,R)-2,6-dimethyldihydro-2H-pyran-4(3H)-one is reported. Key to this strategy is the Ti(OiPr)4-catalyzed Kulinkovich cyclopropanation of silyl protected (R)-ethyl 3-hydroxybutanoate, and subsequent oxidative fragmentati
Anaerobic nitroxide-catalyzed oxidation of alcohols using the NO +/NO· redox pair
Holan, Martin,Jahn, Ullrich
supporting information, p. 58 - 61 (2014/01/23)
A new method for alcohol oxidation using TEMPO or AZADO in conjunction with BF3·OEt2 or LiBF4 as precatalysts and tert-butyl nitrite as a stoichiometric oxidant has been developed. The system is based on a NO+/NO· pair for nitroxide reoxidation under anaerobic conditions. This allows the simple, high-yielding conversion of various achiral and chiral alcohols to carbonyl compounds without epimerization and no formation of nonvolatile byproducts.
Kinetic resolution of chiral cyclohex-2-enones by rhodium(I)/binap- catalyzed 1,2- and 1,4-additions
Kolb, Andreas,Hirner, Sebastian,Harms, Klaus,Zezschwitz, Paultheo Von
supporting information; experimental part, p. 1978 - 1981 (2012/06/18)
The feasibility of kinetic resolutions of racemic monosubstituted cyclohex-2-enones by Rh/binap-catalyzed reactions was investigated. 1,2-Addition of AlMe3 to the 5-substituted derivatives furnished allylic alcohols in the matched case, while t
Synthesis of syn-4,6-dimethyldodecanal, the male sex pheromone and trail-following pheromone of two species of the termite Zootermopsis
Ghostin,Bordereau,Braekman
scheme or table, p. 560 - 568 (2011/05/12)
Recently, we reported that syn-4,6-dimethyldodecanal is the male sex pheromone and the trail-following pheromone of the Termopsidae Zootermopsis nevadensis and Zootermopsis angusticollis. In this article, we describe the syntheses of the mixture of the fo
Stereochemical preference of yeast epoxide hydrolase for the O-axial C3 epimers of 1-oxaspiro[2.5]octanes
Weijers, Carel A. G. M.,Koenst, Paul M.,Franssen, Maurice C. R.,Sudhoelter, Ernst J. R.
, p. 3106 - 3114 (2008/04/01)
The 1-oxaspiro[2.5]octane moiety is a common motif in many biologically active spiroepoxide compounds. Stereochemistry plays an important role in the action of these spiroepoxides, since the O-axial C3 epimers are predominantly responsible for biological
Total synthesis of (±)-arohynapene B
Sugimura, Hideyuki,Uchida, Yuki
, p. 352 - 353 (2007/10/03)
The total synthesis of (±)-arohynapene B, an anticoccidial agent isolated from the fermentation broth of a fungal strain, has been achieved. The tetrahydronaphthalene ring was constructed by the Diels-Alder reaction between dimethyl acetylenedicarboxylate
Palladium-catalyzed intramolecular hydroalkylation of alkenyl- β-keto esters, α-aryl ketones, and alkyl ketones in the presence of Me 3SiCl or HCI
Han, Xiaoqing,Wang, Xiang,Pei, Tao,Widenhoefer, Ross A.
, p. 6333 - 6342 (2007/10/03)
Reaction of 3-butenyl β-keto esters or 3-butenyl α-aryl ketones with a catalytic amount of [PdCl2(CH3CN)2] (2) and a stoichiometric amount of Me3SiCl or Me3SiCl/ CuCl2 in dioxane at 25-70°C formed 2-substituted cyclohexanones in good yield with high regioselectivity. This protocol tolerated a number of ester and aryl groups and tolerated substitution at the allylic, enolic, and cis and trans terminal olefinic positions. In situ NMR experiments indicated that the chlorosilane was not directly involved in palladium-catalyzed hydroalkylation, but rather served as a source of HCl, which presumably catalyzes enolization of the ketone. Identification of HCl as the active promoter of palladium-catalyzed hydroalkylation led to the development of an effective protocol for the hydroalkylation of alkyl 3-butenyl ketones that employed sub-stoichiometric amounts of 2, HCl, and CuCl2 in a sealed tube at 70°C.
Palladium-catalyzed cyclization of alkenyl β-keto esters in the presence of chlorotrimethylsilane
Pei, Tao,Widenhoefer, Ross A.
, p. 650 - 651 (2007/10/03)
PdCl2(CH3CN)2 catalyzed the cyclization of alkenyl β-keto esters in the presence of a stoichiometric amount of SiMe3Cl to form 2-carboalkoxycyclohexanones in good yield with excellent regioselectivity.
