62497-24-9Relevant academic research and scientific papers
Application and scope of Schreiber's gold(I)-catalyzed α-pyrone synthesis to ring a aromatic podolactones
Sánchez-Larios, Eduardo,Giacometti, Robert D.,Hanessian, Stephen
supporting information, p. 5664 - 5669 (2014/11/08)
Schreiber's gold(I)-catalyzed synthesis of α-pyrones was adapted to the total synthesis of a ring A aromatic podolactone, urbalactone. The scope of the acetylenic ester partner in the formation of α-pyrones was studied. The total synthesis features, as ke
Synthesis and biological activities of new furo[3,4-b]carbazoles: Potential topoisomerase II inhibitors
Hajbi, Youssef,Neagoie, Cléopatra,Biannic, Bérenger,Chilloux, Aurélie,Vedrenne, Emeline,Baldeyrou, Brigitte,Bailly, Christian,Mérour, Jean-Yves,Rosca, Sorin,Routier, Sylvain,Lansiaux, Amélie
experimental part, p. 5428 - 5437 (2010/12/25)
New 1,5-Dihydro-4-(substituted phenyl)-3H-furo[3,4-b]carbazol-3-ones were synthesised via a key step Diels-Alder reaction under microwave irradiation. 3-Formylindole was successfully used in a 6-step synthesis to obtain those complex heterocycles. The Diels-Alder reaction generating the carbazole ring was optimised under thermal conditions or microwave irradiation. After cleavage of functional groups, DNA binding, topoisomerase inhibition and cytotoxic properties of the new-formed furocarbazoles were investigated. These carbazoles do not present a strong interaction with the DNA, and do not modify the relaxation of the DNA in the presence of topoisomerase I or II except for one promising compound. This compound is a potent topoisomerase II inhibitor, and its cellular activity is not moderated compared to etoposide. The synthesis of these molecules allowed the generalisation of the method using indole and 5-OBn indole and several benzaldehydes. The synthesis of these molecules produced chemical structures endowed with promising cytotoxic and topoisomerase II inhibition activities.
Total synthesis of (+)-lithospermic acid by asymmetric intramolecular alkylation via catalytic C-H bond activation
O'Malley, Steven J.,Tan, Kian L.,Watzke, Anja,Bergman, Robert G.,Ellman, Jonathan A.
, p. 13496 - 13497 (2007/10/03)
The total synthesis of (+)-lithospermic acid is described. The efficient synthesis features an asymmetric alkylation via C-H bond activation to assemble the dihydrobenzofuran core of the natural product. This was accomplished via a chiral imine-directed C
Oxidation of aromatic compounds: XII. Regio- and stereoselective oxidative dimerization of alkyl 3-arylpropynoates in the system CF3CO 2H-CH2Cl2-PbO2
Savechenkov,Vasil'ev,Rudenko
, p. 1279 - 1283 (2007/10/03)
Regio- and stereoselective oxidative dimerization of alkyl 3-arylpropynoates in the system CF3CO2H-CH 2Cl2-PbO2 (1-30 h, 0-20°C) leads to dialkyl (E)-2,3-bis(arylcarbonyl)-2-butene-1,4-dioates with trans arrangement of the substituents at the double bond.
Preparation of Arylpropiolate Esters from Trichlorocyclopropenium Cation and Elaboration of the Esters to Unsymmetrical 1,4-Pentadiyn-3-ones and Unsymmetrical Tellurapyranones
Wadsworth, Donald H.,Geer, Susan M.,Detty, Michael R.
, p. 3662 - 3668 (2007/10/02)
The addition of aromatic compounds including thiophene, naphthalene derivatives, and some benzene derivatives to trichlorocyclopropenium cation gave nearly quantitative yields of 1-aryl-2,3,3-trichlorocyclopropenes.Alcoholysis of the cyclopropene derivatives gave either arylpropiolate esters or arylpropiolate orthoesters (in the presence of added amine base).The arylpropiolates can be converted to unsymmetrical 1,4-pentadiyn-3-ones by two different approaches.The first approach involved reduction of the arylpropiolate esters with diisobutylaluminum hydride to give the corresponding propargyl alcohol.Pyridinium chlorochromate or manganese dioxide oxidation of the alcohol gave the propargyl aldehydes.Addition of a lithium acetylenide gave a 1,4-pentadiyn-3-ol, which could then be oxidized to the 1,4-pentadiyn-3-one with 10percent chromic acid or manganese dioxide.The second pathway used a Lewis acid mediated coupling of a propargylic acid chloride with a (trimethylsilyl)acetylene to give the 1,4-pentadiyn-3-ones directly.The coupling of 2-thiophenepropiolic acid chloride gave the product of HCl addition to the expected 1,4-diynone.The regiochemistry of addition was determined to be chloride addition to the thiophene-bearing triple bond on the basis of 1H NMR studies.The diynones were converted to unsymmetrical 2,6-disubstituted tellura-4H-pyran-4-ones with disodium telluride anion.
