53544-45-9Relevant academic research and scientific papers
A Radical-Polar Crossover Annulation to Access Terpenoid Motifs
Thomas, William P.,Schatz, Devon J.,George, David T.,Pronin, Sergey V.
supporting information, p. 12246 - 12250 (2019/08/27)
A new catalytic radical-polar crossover annulation between two unsaturated carbonyl compounds is described. The annulation proceeds under exceptionally mild conditions and provides direct and expedient access to complex terpenoid motifs. Application of this chemistry allows for synthesis of forskolin, a densely functionalized terpenoid, in 14 steps from commercially available material.
Rhodium-catalyzed hydrocarbonylation of a homoallylamine via n-h activation and application for synthesis of yohimbane alkaloids
Chiou, Wen-Hua,Wang, Yu-Wei,Kao, Chien-Lun,Chen, Po-Chou,Wu, Chen-Chang
supporting information, p. 4240 - 4244 (2014/11/26)
We describe syntheses of n-yohimbane and alloyohimbane using Rh-catalyzed hydrocarbonylation, which provides a practical methodology to synthesize a δ-lactam from a secondary homoallyl amine. We have also observed an unexpected transformation where the am
Pd(II)-catalyzed intramolecular amidoarylation of alkenes with molecular oxygen as sole oxidant
Yip, Kai-Tai,Yang, Dan
supporting information; experimental part, p. 2134 - 2137 (2011/06/19)
Stereoselective palladium-catalyzed synthesis of structurally versatile indoline derivatives, using molecular oxygen as the sole oxidant, is described. New C-N and C-C bonds form across an alkene in an intramolecular manner. The C-N bond-forming step proceeds via a syn-amidopalladation pathway. The moderate kinetic isotope effects (intramolecular KIE = 3.56) suggest that electrophilic aromatic substitution occurs in the arylation step.
Copper-carbene complexes as catalysts in the synthesis of functionalized styrenes and aliphatic alkenes
Lebel, Helene,Davi, Michael,Diez-Gonzalez, Silvia,Nolan, Steven P.
, p. 144 - 149 (2007/10/03)
(NHC)-Cu (NHC = N-heterocyclic carbene) complexes efficiently catalyzed the methylenation of a variety of aliphatic and aromatic aldehydes and ketones in the presence of trimethylsilyldiazomethane, triphenylphosphine, and 2-propanol. The copper catalysts are not only inexpensive compared to rhodium complexes, but they also exhibit better functional group compatibility with aromatic aldehydes and ketones. Indeed very high yields were obtained for the formation of styrenes containing nitro, trifluoromethyl, amino, and ester groups, as well as for pyridine-, pyrrole-, and indole-substituted alkenes.
Intermolecular photoreaction of benzenecarbothioamide with γ, δ-unsaturated ketones: Application to synthesis of cycloalkane [c]-fused pyridines
Oda, Kazuaki,Haneda, Michiko,Nishizon, Naozumi,Machida, Minoru
, p. 563 - 566 (2007/10/03)
Irradiation of benzenecarbothioamide with (2-methylene-cycloalkyl)acetaldehyde in benzene gives cycloalkane [c]-fused pyridines in moderate yields.
Studies toward total synthesis of non-aromatic Erythrina alkaloids. (1) Synthesis and isomerization of unsaturated bicyclic δ-lactones
Tsuda,Ishiura,Takamura,Hosoi,Isobe,Mohri
, p. 2797 - 2802 (2007/10/02)
As a model of the C/D ring system of erythroidines, bicyclic unsaturated δ-lactones were synthesized in a regio-selective manner, and their isomerization reactions in the presence of acid, base (DBU, 1,8-diazabicyclo-[5.4.0]undec-7-ene), and NaOH were stu
Reductive, Radical-Induced Cyclizations of 5-Hexenals as a Biomimetic Model of the Chemistry of Secologanin Formation
Ikeda, Takafumi,Yue, Stephen,Hutchinson, C. Richard
, p. 5193 - 5199 (2007/10/02)
A model reaction for studying the mechanism of the biological conversion of the iridoid loganin (1) to the secoiridoid secologanin (2) is the reductive, radical-induced cyclization of secologanin tetraacetate (4) to loganin tetraacetate.Treatment of 4 with Mg and Me3SiCl in THF at room temperature gives a mixture of the four possible C-6 and C-7 epimers of loganin tetraacetate in which the natural stereochemistry predominates.This result suggests that the biochemical event, which involves cleavage of the C-6 and C-7 bond of 1 in forming 2, may be a homolytic process that is initiated by formation of a carbon radical at C-8.The scope of the cyclization reaction, which formally occurred in a 5-hexanal moiety in 4, is defined by studies of the cyclization of six other δ,ε-unsaturated aldehydes.The results illustrate a new way for ring annulation through the reductive, radical-induced cyclization of δ,ε-unsaturated aldehydes.
Copper(I) Catalysis of Olefin Photoreactions. 10. Synthesis of Multicyclic Carbon Networks by Photobicyclization
Salomon, Robert G.,Ghosh, Subrata,Zagorski, Michael G.,Reitz, Michael
, p. 829 - 836 (2007/10/02)
The synthetic utility of copper-catalyzed photobicyclization for construction of tricyclic ring systems is explored.UV irradiation of several monocyclic β- and γ-(4-pentenyl)allyl alcohols in the presence of copper(I) trifluoromethanesulfonate (CuOTf) gen
THE SPIROOXIRANE ROUTE TO TRANS-FUSED γ-LACTONES
Strekowski, Lucjan,Battiste, Merle A.
, p. 279 - 282 (2007/10/02)
Convenient access to trans-fused γ-lactones is provided by sodium benzenethiolate promoted ring opening of appropriate γ,δ-spiroepoxyesters.
