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

J Org Chem. 2021 Apr 16;86(8):6025-6029. doi: 10.1021/acs.joc.1c00390. Epub 2021 Mar 26.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols
  • Alkaloids*
  • Amines*
  • Catalysis
  • Stereoisomerism

Substances

  • Alcohols
  • Alkaloids
  • Amines