Enantioselective, Convergent Synthesis of the Ineleganolide Core by a Tandem Annulation Cascade.

ABSTRACT: An enantioselective and diastereoselective approach toward the synthesis of the polycyclic norditerpenoid ineleganolide is disclosed. A palladium-catalyzed enantioselective allylic alkylation is employed to stereoselectively construct the requisite chiral tertiary ether and facilitate the synthesis of a 1,3-cis-cyclopentenediol building block. Careful substrate design enabled the convergent assembly of the ineleganolide [6,7,5,5]-tetracyclic scaffold by a diastereoselective cyclopropanation-Cope rearrangement cascade under unusually mild conditions. Computational evaluation of ground state energies of late-stage synthetic intermediates was used to guide synthetic development and aid in the investigation of the conformational rigidity of these highly constrained and compact polycycli

SUBMITTER: Craig RA 

PROVIDER: S-EPMC5321630 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature