Diastereospecific arylation and cascade deconstructive amidation/thioesterification of readily available lactam-fused bromolactones.

ABSTRACT: An intrinsic goal when designing synthetic methodology is to identify approaches whereby readily accessible precursors are converted into an array of products, which efficiently tap into new 3D-chemical space. In these studies, readily available bicyclic lactam-bromolactones have been interrogated in several fragment growth protocols by utilizing the halogen and lactone motifs as versatile linchpins for strategic construction of C-C, C-N, C-O, and C-S bonds. Diastereospecific C(sp³)-C(sp²) Kumada coupling of sterically imposing [5,5]-bicyclic lactam-bromolactones with several aryl Grignard reagents, under palladium catalysis, furnishes diarylmethane-tethered lactam-lactones in synthetically attractive yields, stereoinvertive fashion, and with a tolerance for many func

SUBMITTER: Do M 

PROVIDER: S-EPMC10463012 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature