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

The Journal of Organic Chemistry
2021.0

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 alpha-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.

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