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

Qu, Chunlei; Long, Xianwen; Sang, Yueqian; Zhang, Min; Zhao, Xiaoli; Xue, Xiao-Song; Deng, Jun

doi:10.1021/acs.orglett.0c02865.s001

ol0c02865_si_001.pdf (6.89 MB)

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

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.