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Relevant academic research and scientific papers

Ruthenium-Catalyzed (Z)-Selective Hydroboration of Terminal Alkynes with Naphthalene-1,8-diaminatoborane

The metal-catalyzed (Z)-selective hydroboration of terminal alkynes is synthetically challenging due to the usually (E)-selective nature of the hydroboration and the formation of the thermodynamically unstable (Z)-isomer. Herein, we report that N-heterocyclic-carbene-ligated ruthenium complexes catalyze the (Z)-selective hydroboration of terminal alkynes with H-B(dan) (dan = naphthalene-1,8-diaminato), which generates a diverse range of synthetically valuable (Z)-alkenylboranes. Mechanistic studies, particularly the isolation of a catalytically relevant borylruthenium complex, revealed a mechanism that involves the insertion of the alkyne into a Ru-B bond, which provides a catalytic cycle that is distinctly different from that of previously reported (Z)-selective hydroborations. The direct cross-coupling of the obtained (Z)-alkenyl-B(dan) enables the rapid synthesis of biologically active Combretastatin A-4 analogues.

Synthesis and insect antifeedant activity of stilbene derivatives against Brontispa longissima Larvae

Continuing our search for natural product-based compounds for the control of B. longissima Larvae, 25 stilbene analogs were synthesized and evaluated for insect antifeedant activity against third-instar larvae of B. longissima for the first time. Among all the tested compounds, especially compounds 3a, 3c, and 6 showed pronounced antifeedant activities with AFC50 values of 0.218, 0.327, and 0.226 mg/mL, respectively. The different antifeedant activity ranges of these compounds indicated that variation of chemical structures in the stilbene skeleton markedly affected the activity profiles of this compound class, and some important SAR information has been revealed from it. In addition, to understand the structural requirements for antifeedant activities of the 25 synthesized stilbene analogs, a comparative molecular field analysis (CoMFA) model, which yielded the leave-one-out (LOO) cross-validated correlation coefficient (q 2) of 0.533 and a non-cross-validated correlation coefficient (r 2) of 0.929, was constructed. Together, these preliminary results may be useful in guiding further modification of stilbenes in the development of potential new antifeedants.

An efficient microwave-promoted route to (Z)-stilbenes from trans-cinnamic acids: Synthesis of combretastatin A-4 and analogues

cis-Stilbenes were synthesized from trans-cinnamic acids, involving ethylenic-bond bromination and a subsequent one-pot microwave-promoted stereoselective debrominative decarboxylation-Suzuki cross-coupling strategy. This sequence represents a useful way to prepare a variety of combretastatin A-4 derivatives.

Sythesis of 2,2'-Diacyl-1,1'-biaryls. Regiocontrolled Protection of Ketones in Unsymmetrically Substituted 9,10-Phenanthrenequinones

A regiocontrolled monoketalization of unsymmetrically substituted phenanthrenequinones by use of 2,2-dimethyl-1,3-propanediol as the ketalizing reagent has been effected with the help of bromo substitution in one of the aromatic rings at the C-1 or C-8 po