Biomimetic Total Synthesis of (±)-Carbocyclinone-534 Reveals Its Biosynthetic Pathway
Chunlei Qu, Xianwen Long, Yueqian Sang, Min Zhang, Xiao‐Li Zhao, Xiao‐Song Xue, Jun Deng
Abstract
Carbocyclinone-534 is a new antibiotic produced after the metabolism of tapinarof. We identify a biomimetic total synthesis of carbocyclinone-534 in eight steps by taking advantage of an intermolecular Diels-Alder homodimerization/dehydrogenation/intramolecular Diels-Alder cycloaddition cascade. This synthetic sequence provides direct experimental evidence for revealing the biosynthetic pathway of carbocyclinone-534.
Topics & Concepts
ChemistryIntramolecular forceCycloadditionDehydrogenationIntermolecular forceTotal synthesisCascadeCombinatorial chemistryStereochemistryBiosynthesisOrganic chemistryMoleculeEnzymeCatalysisChromatographyMicrobial Natural Products and BiosynthesisMarine Sponges and Natural ProductsChemical synthesis and alkaloids