Synthesis and biological evaluation of phenolic 4,5-dihydroisoxazoles and 3-hydroxy ketones as estrogen receptor α and β agonists

Catalytic Enantioselective Iodoetherification of Oximes

“…[9] Isoxazolines are an important class of com-pounds found in several biologically active agents and versatile intermediates in organic synthesis. [10] In spite of their utility in chemistry and biology, there is no report on the enantioselective synthesis of isoxazolines containing a quaternary stereogenic center. Our method offers a straightforward access to enantioenriched D 2 -isoxazolines containing a quaternary stereogenic center (Scheme 2).…”

Selective C−C Coupling of Vinyl Epoxides with Diborylmethide Lithium Salts

“…The added value of the regio‐ and diastereoselective ring opening/C−C cross‐coupling of 3,4‐epoxy‐1‐cyclohexene with Li [RC(Bpin) 2 ] [R=(trimethylsilyl)methyl group] allowed for the in situ oxidative workup towards 2‐[hydroxy(trimethylsilyl)methyl]cyclohex‐3‐en‐1‐ol ( 39 ) as a single diastereoisomer with full retention of the configuration (Scheme ). The consecutive ring opening/ring closure of substrate 2‐methyl‐2‐vinyloxirane when reacts with diborylmethide lithium salts 22 , generates the 3‐borylated 1,2‐oxaborolan‐2‐ol product 31 , which under oxidative workup conditions ends up in the formation of polyfunctional allylic alcohol 5‐hydroxy‐5‐methyl‐1‐phenylhept‐6‐en‐3‐one ( 40 ), containing a tertiary β‐hydroxyl group, characteristic of high therapeutic value (Scheme ).…”

Substituent effect study on experimental 13C NMR chemical shifts of (3-(substituted phenyl)-cis-4,5-dihydroisoxazole-4,5-diyl)bis(methylene)diacetate derivatives

“…Isoxazole derivatives are a class of heterocyclic compounds having a wide a range of properties such as immunosuppressive [1], antimicrobial [2,3] antibacterial [4], antioxidant and anti-inflammatory [5], cytotoxic [6], antimycobacterial [7], analgesic [8], muscarinic [9], antitubulin [10], anticoagulant [11], antituberculosis [12] activities, anticancer [13,14], DNA-intercalating [15], antiproliferative [16] agents, firefly luciferase (Luc) [17], human transglutaminase 2 [18] inhibitors, estrogen receptor a and b agonists [19]. 4,5-Dihydroisoxazoles are useful intermediates in organic synthesis such as synthesis of b-hydroxy ketones, c-amino alcohols, a, b-unsaturated oximes, and b-hydroxy nitriles [20][21][22][23][24][25][26][27].…”