Stereocontrolled synthesis of (+)-lycoperdic acid based on a palladium catalyzed reaction using a serine-derived organozinc reagent

A Highly Stereocontrolled Total Synthesis of (−)-Neodysiherbaine A

“…Our synthetic plan is illustrated in Scheme . Based on the methodology we have demonstrated in the total synthesis of dysiherbaine 4a and lycoperdic acid, we envisaged allylic alcohol 4 as a precursor of neodysiherbaine A ( 2 ), which would be accessible via a cross-coupling reaction of alkenyl iodide 6 and organozinc reagent 5 . We assumed that the C4 quaternary stereogenic center would be assembled in stereocontrolled manner via Katsuki−Sharpless asymmetric epoxidation of 4 followed by 5-exo-tet cyclization of 3 with inversion of the configuration.…”

Catalytic Enantioselective Total Synthesis of (+)–Lycoperdic Acid

“…To date, there are seven total syntheses and one formal synthesis for (+)- 1 . − Most of them rely on either chiral pool or chiral auxiliaries to set the stereochemistry at C2 and C4 (Figure ). Very recently, the Oikawa group disclosed an approach where catalytic enantioselective hydrogenation was used to control the stereochemistry at C2 of (+)- 1 , but the construction of C4 was not stereoselective …”