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

Abstract

The common, key tricyclic core of stemona alkaloids parvistemonine (1) and parvistemoline (2), 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.