Synthetic Studies toward Parvistemoline Using Asymmetric Ir/Amine-Catalyzed Allylation.

The common, key tricyclic core of stemona alkaloids parvistemonine () and parvistemoline (), whose synthetic efforts have not reported yet, was constructed through a new strategy in which three contiguous stereogenic centers were set by using Carreira's asymmetric Ir/amine-catalyzed allylation of aldehyde with α-vinylfurfuryl alcohol and Ellman's sulfinamide chiral auxiliary, respectively. The furan ring was especially designed to act as the precursor of the butyrolactone while establishing the significant chirality.

Asymmetric Total Syntheses of (-)-Fennebricin A, (-)-Renieramycin J, (-)-Renieramycin G, (-)-Renieramycin M, and (-)- Jorunnamycin A via C-H Activation.

Collective total synthesis of five tetrahydroisoquinoline alkaloids including the first total synthesis of (-)-fennebricin A and (-)-renieramycin J has been accomplished. The synthesis features employing a single common amino acid to symmetrically construct the pentacycle of title alkaloids. The palladium-catalyzed arylation of alanine-derived amide developed by Yu was tactically utilized to afford unnatural amino acid building block rapidly and practically.