Streamlined Strategy for Scalable and Enantioselective Total Syntheses of the Eburnane Alkaloids
Gujjula V. Ramakrishna, Larisa P. Pop, Zurwa Latif, Harish K. V. Suryadevara, L.L.do E. Santo, Filippo Romiti
Abstract
A general, concise, and efficient strategy for the enantioselective synthesis of the eburnane alkaloid family of natural products is disclosed. Specifically, 13 members of the natural product family were prepared from commercially available and inexpensive starting materials. The brevity and modularity of the route are largely on account of a two-phase synthesis logic and a key catalytic enantioconvergent cross-coupling to establish the C20 stereogenic center. The strategies described here are expected to facilitate in-depth biological studies and provide access to new anticancer eburnane analogues.
Topics & Concepts
Enantioselective synthesisChemistryStereocenterNatural productTotal synthesisModularity (biology)Combinatorial chemistryStereochemistryCatalysisOrganic chemistryBiologyGeneticsAlkaloids: synthesis and pharmacologyChemical synthesis and alkaloidsMicrobial Natural Products and Biosynthesis