Application of oxygen/nitrogen substituted donor-acceptor cyclopropanes in the total synthesis of natural products

Total Synthesis of Lophirone F Hexamethyl Ether

“…Substituted tetrahydrofurans, the substructures frequently found in a broad array of natural products and other biologically active molecules, often exhibit a diverse range of beneficial therapeutic properties such as antitumor, antihelmic, antimalarial, antimicrobial, and antiprotozoal . The syntheses of these molecules have attracted considerable effort toward the development of synthetic methods for the stereoselective construction of substituted tetrahydrofurans …”

Donor‐Acceptor Cyclopropanes in the Synthesis of Carbocycles

“…To underline the unusual reactivity of such cyclopropanes, Reissig proposed to refer them as "donor-acceptor-substituted cyclopropanes" [1] that was later reduced to donor-acceptor (D-A) cyclopropanes. [2] Initially cyclopropanes with heteroatom-based donor (R 2 NÀ, ROÀ, RSÀ) and carbonyl (ketone, ester, amide, etc.) or cyano acceptor groups were considered as typical D-A cyclopropanes.…”

“…These substrates have been also found to react as synthetic equivalents of alkylidene malonates . Based on these advances, total syntheses of diverse natural products from D‐A cyclopropanes have been developed . With all these achievements in mind, Werz and co‐authors have characterized this period as “A new golden age for donor‐acceptor cyclopropanes” .…”

Stereoselective Synthesis of Cyclopropylidene Iminolactones and Functionalized Cyclopropanecarboxamides Mediated by Triflic Acid

“…Densely functionalized cyclopropanes, in particular cyclopropanecarboxamides, are very important as biologically active substances, as well as versatile building blocks in organic synthesis. Their unique structural features combined with distinct reactivity modes have found application in various fields, including chemical biology and medicinal chemistry .…”