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

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

Journal: Organic letters 2021;22(24):9421-9426

PMID: 33086787

Full Text on American Chemical Society View on PubMed

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.

Address: State 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.; University of Chinese Academy of Sciences, Beijing 100049, China.; State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.; University of Chinese Academy of Sciences, Beijing 100049, China.; State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.; State 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.

DOI: 10.1021/acs.orglett.0c02865

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https://doi.org/10.1021/acs.orglett.0c02865

MeSH Terms: Biomimetics, Biosynthetic Pathways, Cycloaddition Reaction, Dimerization, Molecular Structure, Stereoisomerism