96641-44-0Relevant academic research and scientific papers
Hydroxymethylation enantioselective d'alkyl benzenes chrome tricarbonyle ortho substitues
Lebibi,Pelinski,Maciejewski,Brocard
, p. 6011 - 6020 (1990)
Benzylic hydroxymethylation of chiral ortho alkyloxy, or dialkylamino, alkyl benzene tricarbonylchromium was found to show high or complete diastereoselectivity. Resolution of ortho methoxy ethyl benzene tricarbonylchromium provided (-)-(R)-2-(orthomethox
Enantioselective Synthesis of 4-Methyl-3,4-dihydroisocoumarin via Asymmetric Hydroformylation of Styrene Derivatives
Qu, Bo,Tan, Renchang,Herling, Madison R.,Haddad, Nizar,Grinberg, Nelu,Kozlowski, Marisa C.,Zhang, Xumu,Senanayake, Chris H.
, p. 4915 - 4920 (2019/03/19)
Enantioenriched aldehydes are produced through asymmetric hydroformylation of styrene derivatives using BIBOP-type ligands. The featured example is enantioselective synthesis of 4-methyl-3,4-dihydroisocoumarin, which was prepared in a 95.1:4.9 enantiomeric ratio from asymmetric hydroformylation of ethyl 2-vinylbenzoate followed by in situ lactonization during the reduction process. The conditions are compatible with both electron-rich and electron-poor substituents.
Catalytic asymmetric couplings of ketenes with aldehydes to generate enol esters
Schaefer, Carsten,Fu, Gregory C.
, p. 4606 - 4608 (2007/10/03)
(Chemical Equation Presented) With a little help from the ferrocenyl catalyst ((-)-1), a wide array of α-arylalkanoic acid derivatives can be produced from the catalytic asymmetric coupling of ketenes with aldehydes (see scheme). The enol esters are readily transformed into other useful families of compounds such as carboxylic acids and alcohols.
Potent Kv1.3 inhibitors from correolide - Modification of the C18 position
Bao, Jianming,Miao, Shouwu,Kayser, Frank,Kotliar, Andrew J.,Baker, Robert K.,Doss, George A.,Felix, John P.,Bugianesi, Randal M.,Slaughter, Robert S.,Kaczorowski, Gregory J.,Garcia, Maria L.,Ha, Sookhee N.,Castonguay, Laurie,Koo, Gloria C.,Shah, Kashmira,Springer, Marty S.,Staruch, Mary Jo,Parsons, William H.,Rupprecht, Kathleen M.
, p. 447 - 451 (2007/10/03)
Correolide (1) was converted to a new series of tetracyclic Kv1.3 blockers 2. SAR for this class of compounds in two functional assays, Rb_Kv and human T cell proliferation, is presented herein. Kv1.3, the voltage-gated potassium channel in human T cells, represents a new target for treating immunosuppression and autoimmune diseases. Correolide (1), a pentacyclic natural product, is a potent and selective Kv1.3 channel blocker. Simplification of correolide via removal of its E-ring generates enone 4, whose modification produced a new series of tetracyclic Kv1.3 blockers. The structure-activity relationship for this class of compounds in two functional assays, Rb_Kv and human T cell proliferation, is presented herein. The most potent analog 43 is 15-fold more potent than correolide as inhibitor of human T cell proliferation.
The Total Synthesis of (15R)- and (15S)-16-Hydroxyferruginol
Matsumoto, Takashi,Imai, Sachihiko,Miuchi, Shigekazu,Sugibayashi, Hidenori
, p. 340 - 345 (2007/10/02)
In order to assign the absolute configuration of C-15 in natural 16-hydroxyferruginol, (5S,10S,15R)-(1a) and (5S,10S,15S)-8,11,13-abietatriene-12-16-diol (1b) have been synthesized.Optical resolution of 2-(2-methoxyphenyl)propanoic acid, prepared from methyl (2-methoxyphenyl)acetate, with cinchonidine afforded (R)- and (S)-enantiomers, which were converted into triphenylphosphonium chloride (3a) and its (S)-isomer (3b) respectively.The Wittig reaction of (R)-(-)-α-cyclocitral with 3a, followed by partial catalytic hydrogenation and intramolecular cyclization gave (5S,10S,15R)-12,16-dimethoxy-8,11,13-abietatriene (16a) together with its (5S,10R,15R)-isomer.Similary, 3b was also converted into (5S,10S,15S)-12,13-dimethoxy-8,11-abietatriene (6b) and its (5S,10R,15R)-isomer.Demethylation of 16a gave 1a which was identical with natural 16-hydroxyferruginol.The dimethoxy compound 16b was also demethylated to give 1b.
