Chiral γ-lactones are prevalent organic architectures found in a large array of natural products. In this work, we disclose the development of a modified catalytic system utilizing a commercially available Cu-phosphite catalyst for the diastereoselective reductive coupling of chiral allenamides and ketones to afford chiral γ-lactone precursors in 80:20 to 99:1 dr.

Pd-catalyzed allylic alkylation of C-based nucleophiles using both chiral and achiral allenamides is described. High yields were obtained to provide synthetically valuable (E)-enamide products in high E : Z-selectivity while generating a quaternary carbon atom. Some potential stereocontrolled applications of the resultant (E)-enamide functionality are described.

A concise and practical synthesis has been developed to provide the 8-fluoro-5-hydroxy-3,4-diydrocarbostyril (8-FDC) fragment of OPC-167832 in 41 % yield and in > 99 % purity over 4 steps from 3-amino-4-fluorophenol. The key feature of this process is the development of a telescoped one pot synthesis of the quinolone via a chemoselective amidation and easier product isolation without the need for a column chromatography.

Chiral g-lactones are prevalent organic architectures found in a large array of natural products. In this work, we disclose the development of a modified catalytic system utilizing a commercially available Cu-phosphite catalyst for the diastereoselective reductive coupling of chiral allenamides and ketones to afford chiral -lactone precursors in 80:20 to 99:1 dr.

A concise and practical synthesis has been developed to provide the 8-fluoro-5-hydroxy-3,4-diydrocarbostyril ( 8-FDC ) fragment of OPC-167832 in 41% yield and in >99% purity over four steps from 3-amino-4-fluorophenol. The key feature of this process is the development of a telescoped one-pot synthesis of the quinolone via a chemoselective amidation/acid-induced cyclization that allows for simple product isolation without the need for column chromatography.