Pd-Catalyzed Three-Component Reaction of 3‑(Pinacolatoboryl)ally Acetates, Aldehydes, and Organoboranes: A New Entry to Stereoselective Synthesis of (<i>Z</i>)-<i>anti</i>-Homoallylic Alcohols

The Pd-catalyzed three-component reaction of 3-(pinacolato­boryl)­allyl acetates, aldehydes, and organoboranes is described. The reaction is initiated by the formation of an allylic <i>gem</i>-palladium/boryl intermediate, which then undergoes allylation of aldehydes by allylboronates followed by a coupling reaction of in situ generated (<i>Z</i>)-vinylpalladium acetates with organoboranes to provide the (<i>Z</i>)-<i>anti</i>-homoallylic alcohols with high levels of diastereoselectivity and alkene stereocontrol

Practical and Convenient Synthesis of 1,6-Di- or 1,2,5,6-Tetra-arylhexa-1,3,5-trienes by the Dimerization of Pd(0)-Complexed Alkenylcarbenes Generated from π‑Allylpalladium Intermediates

Pd­(0)-complexed 3-aryl or 2,3-diaryl propenylcarbenes generated from α-silyl-, α-germyl-, or α-boryl-σ-allylpalladium intermediates undergo self-dimerization to provide 1,6-di- or 1,2,5,6-tetraarylhexa-1,3,5-trienes in good to high yields. This method allows the use of a π-allylpalladium intermediate for a carbenoid precursor. Furthermore, the obtained 1,2,5,6-tetraarylhexa-1,3,5-trienes exhibit aggregation-induced emission enhancement property

Controllable Stereoselective Synthesis of (<i>Z</i>)<i>-</i> and (<i>E</i>)‑Homoallylic Alcohols Using a Palladium-Catalyzed Three-Component Reaction

Diastereoselective synthesis of (<i>Z</i>)- and (<i>E</i>)-homoallylic alcohols using a Pd-catalyzed three-component reaction of 3-(pinacolatoboryl)­allyl benzoates, aldehydes, and aryl stannanes was developed, which provides an alternative method for the allylboration of aldehydes using α,γ-diaryl-substituted allylboronates. Both sets of reaction conditions enable access to either (<i>Z</i>)- or (<i>E</i>)-homoallylic alcohols with good to high alkene stereocontrol. The present method showed good functional group compatibility and generality. Efficient chirality transfer reactions to afford enantioenriched (<i>Z</i>)- and (<i>E</i>)-homoallylic alcohols were also achieved

Synthesis of Potent and Selective Inhibitors of Aldo-Keto Reductase 1B10 and Their Efficacy against Proliferation, Metastasis, and Cisplatin Resistance of Lung Cancer Cells

Aldo-keto reductase 1B10 (AKR1B10) is overexpressed in several extraintestinal cancers, particularly in non-small-cell lung cancer, where AKR1B10 is a potential diagnostic marker and therapeutic target. Selective AKR1B10 inhibitors are required because compounds should not inhibit the highly related aldose reductase that is involved in monosaccharide and prostaglandin metabolism. Currently, 7-hydroxy-2-(4-methoxyphenylimino)-2<i>H</i>-chromene-3-carboxylic acid benzylamide (HMPC) is known to be the most potent competitive inhibitor of AKR1B10, but it is nonselective. In this study, derivatives of HMPC were synthesized by removing the 4-methoxyphenylimino moiety and replacing the benzylamide with phenylpropylamide. Among them, <b>4c</b> and <b>4e</b> showed higher AKR1B10 inhibitory potency (IC₅₀ 4.2 and 3.5 nM, respectively) and selectivity than HMPC. The treatments with the two compounds significantly suppressed not only migration, proliferation, and metastasis of lung cancer A549 cells but also metastatic and invasive potentials of cisplatin-resistant A549 cells