On the Erosion of Enantiopurity of Rhodonoids via Their Asymmetric Total Synthesis
Hyeju Jeon, Gyumin Kang, Myungjo J. Kim, Ji Soo Shin, Sunkyu Han, Hee‐Yoon Lee
Abstract
Rhodonoid natural products are found in nature as a scalemic mixture. This interesting phytochemical feature is presumed to originate from a reversible electrocyclic ring opening of the chromene core present in the biogenetic precursors of rhodonoids. Herein, we systematically investigated factors that are responsible for this racemization event. This eventually led us to complete the asymmetric total synthesis of rhodonoids A, C, D, and G.
Topics & Concepts
ChemistryRacemizationRing (chemistry)StereochemistryPhytochemicalTotal synthesisEnantioselective synthesisCombinatorial chemistryOrganic chemistryCatalysisBiochemistryPhytochemistry and Biological ActivitiesPhytochemistry and Bioactivity StudiesNatural product bioactivities and synthesis