Synthesis of Polyene Bioactive Natural Products: FR252921 and Vitamin A
Dattatraya H. Dethe, Vimlesh Kumar, Nagabhushana C. Beeralingappa, Kunj B. Mishra, Appasaheb K. Nirpal
Abstract
A formal synthesis of FR252921, a potent macrocyclic immunosuppressive agent, and a six-step synthesis of vitamin A have been demonstrated. The application of a ruthenium-catalyzed step-economic and environmentally benign strategy for the highly stereo- and chemoselective construction of valuable polyene motifs of FR252921 and vitamin A highlights the syntheses. The key features for the synthesis FR252921 include preparation of the triene moiety followed by two consecutive peptide couplings of the three fragments.
Topics & Concepts
PolyeneChemistryMoietyCombinatorial chemistryRutheniumTotal synthesisCatalysisStereochemistryOrganic chemistryMarine Sponges and Natural ProductsMicrobial Natural Products and BiosynthesisChemical Synthesis and Analysis