Biomimetic Total Synthesis of (±)-Carbocyclinone-534 Reveals Its Biosynthetic Pathway
Chunlei Qu1,2, Xianwen Long1,2, Yueqian Sang3,2
1State Key Laboratory of Phytochemistry and Plant Resources in West China and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, 132 Lanhei Road, Kunming 100049, China.
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.
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