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Biomimetic Total Synthesis of (±)-Carbocyclinone-534 Reveals Its Biosynthetic Pathway

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journal contribution
posted on 2020-10-22, 01:43 authored by Chunlei Qu, Xianwen Long, Yueqian Sang, Min Zhang, Xiaoli Zhao, Xiao-Song Xue, Jun Deng
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.