Recent Advances of Applying Boron‐Reagents in Asymmetric Total Syntheses of Natural Products and Bio‐Active Molecules

Abstract

Boron‐reagents are very useful tools in synthetic organic chemistry and have been extensively explored in the asymmetric methodology development. The past decade has witnessed an upsurge of interest in exploring their application in the asymmetric total synthesis. Several synthetic strategies, such as the transmetalation strategy, the boronate ligand exchange strategy, the Lewis base and Brønsted acid activation strategies, and the lithiation‐borylation strategy, offered very powerful platforms for the development of innovative synthetic routes for asymmetric total synthesis. This review highlights the progress (2007–2019) of the application of these synthetic strategies in the asymmetric total synthesis of natural products, and of biologically and medicinally relevant molecules.magnified image

Copper-Catalyzed Enantiotopic-Group-Selective Allylation of gem-Diborylalkanes

“…The development of an efficient catalytic reaction for preparing enantioenriched organoboron compounds received considerable attention over the past decades because they can serve as versatile intermediates in the synthesis of a range of natural products and pharmaceuticals . Thus, various enantioselective approaches to accessing these compounds have been reported including hydrogenation of vinyl boronates, hydroboration, conjugate addition, allylic borylation, and cross-couplings .…”

Synthesis and Reactivity of Allenylboron Compounds

“…[4] For example, allylic and vinyl/aryl organoboron compounds have been widely utilized for allylation, cross-coupling, and many other CÀ C bond-forming reactions. [5] Szabó et al summarized the synthesis and reactivity of allylic boron compounds and put them into recent perspective. [6] Similarly, allenylboron compounds have been widely utilized for CÀ C bond-forming reactions.…”

Synthesis of the Hexahydropyrrolo-[3,2-c]-quinoline Core Structure and Strategies for Further Elaboration to Martinelline, Martinellic Acid, Incargranine B, and Seneciobipyrrolidine

“…Natural products have been and continue to be an immense source of inspiration for organic chemists looking for challenging synthetic targets to test new synthetic strategies and methodologies [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 ]. In addition, natural products are good sources for discovery of novel scaffolds, which is important inspiration for new structural motifs in medicinal chemistry and eventually for drug discovery [ 10 , 11 , 12 ].…”