Asymmetric Synthesis of Scillascillin-Type Homoisoflavonoid

Abstract

The first asymmetric synthesis of a scillascillin-type homoisoflavonoid was reported. Key reactions for the asymmetric synthesis of benzocyclobutene include catalytic reductive desymmetrization of malonic ester and an intramolecular C−H activation of the methyl group.

Advances in the synthesis of rearranged homoisoflavonoids

“…Only in 2024, forty years after the first isolation of scillascillin ( 21 ), this unique spiro-cyclobenzobutene skeleton was obtained in an enantioselective fashion. 106 Ren and coworkers reported the asymmetric synthesis of scillascillin-type homoisoflavonoids using two key-steps: a catalytic reductive desymmetrization of malonic ester to access the benzylic all-carbon quaternary center and an intramolecular C–H activation of methyl group for construction of the four-membered ring (Scheme 34).…”

Copper-Catalyzed Synthesis of Furan-Tethered Benzocyclobutenes via Carbene-Mediated 1,4-Sulfinate Migration-Annulation

“…Ivabradine, for instance, is a clinically prescribed medication that functions as a heart-rate-lowering agent . Scillascillin A, belonging to a structurally fascinating group of homoisoflavonoids, has demonstrated activity against human cancer cell lines, including MCF-7 (breast cancer) and DU-145 (prostate cancer) . Additionally, cropalliflavone B is recognized for its significant contributions to the agricultural sector .…”