38970-47-7Relevant articles and documents
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.
Six- vs seven-membered ring formation from the 1- bicyclo[4.1.0]heptanylmethyl radical: Synthetic and ab initio studies
Kantorowski, Eric J.,Eisenberg, Shawn W. E.,Fink, William H.,Kurth, Mark J.
, p. 570 - 580 (2007/10/03)
The viability of utilizing 1-bicyclo[4.1.0]heptanylmethyl radical (3) to serve as a progenitor of seven-membered carbocycles was examined. Rate constants for the rearrangement of this radical to 3-methylenecycloheptyl radical (4) and 2-methylenecyclohexyl-1-methyl radical (6) were measured using the competition method of 3 with thiophenol over the temperature range of -75 to 59 °C. Arrhenius functions were calculated for the conversions of 3 to 4 and 3 to 6 and found to be log(k/s-1) = (12.38 ± 0.20) - (5.63 ± 0.23)/θ and log(k/s-1) = (11.54 ± 0.32) - (5.26 ± 0.37)/θ, respectively. The rate constants for these conversions at 25 °C are 1.86 x 108 s-1 and 5.11 x 107 s-1, respectively. Hence, the seven-membered ring-expanded carbocycle is formed 3.6 times faster at 25 °C than the nonexpanded species. This suggests that the 1-bicyclo[4.1.0]heptanylmethyl radical system may be synthetically useful in seven-membered ring-forming methodology. Preliminary theoretical examination of this radical system qualitatively predicted the experimentally determined energies of activation: PMP4/6-31G*//HF/6-31G*ΔE(a) (3 → 6 - 3 → 4) = 3.0 kcal/mol with zero point energy correction. The HF/6-31G* optimized reaction coordinate stationary points suggest cyclopropyl substituent eclipsing interactions play an important role in determining the kinetic outcome of these rearrangements.
Synthesis and evaluation of cardiotonic activity of simple butenolides II
Medarde, M.,Caballero, E.,Tome, F.,Garcia, A.,Montero, M.J.,et al.
, p. 887 - 892 (2007/10/02)
Three 3-(2-hydroxy-2-methylcyclohexylmethyl)butanolides were synthesized and checked for inotropic activity.Very weak effects were observed for all of them. cardenolide analogues/ butanolides/ inotropic effects
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
β-hydroxy Esters: (E)- versus (Z)-Enolate Geometry in Dianionic Claisen Rearrangements
Kurth, Mark J.,Beard, Richard L.
, p. 4085 - 4088 (2007/10/02)
Control elements operative in the β-hydroxy ester dianionic Claisen rearrangements are probed.Stereochemistry at Cβ dictates face selectivity at Cα and Cβ' in 1->2-5, but only to the extent that it controls ester enolate g
Chemistry of the Podocarpaceae. LV. Conversion of 8α,13-Epoxylabd-14-en-2-one into 3β-Hydroxy-13,14,15,16-tetranorlabd-8(17)-en-12-oic Acid
Cambie, Richard C.,Leong, Soo H.,Palmer, Brian D.,Preston, Alan F.
, p. 155 - 168 (2007/10/02)
8α,13-Epoxylabd-14-en-2-one (2-oxomanoyl oxide) (1) has been converted into 3β-hydroxy-13,14,15,16-tetranorlabd-8(17)-en-12-oic acid (7), a compound with potential as an optically active intermediate for synthesis.Attempts to couple the acid (7) electroly
