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

doi:10.1021/acs.orglett.0c02865

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

Org Lett. 2020 Dec 18;22(24):9421-9426. doi: 10.1021/acs.orglett.0c02865. Epub 2020 Oct 21.

Authors

Chunlei Qu^{1

2}, Xianwen Long^{1

2}, Yueqian Sang^{3

2}, Min Zhang^{1

2}, Xiaoli Zhao^{1

2}, Xiao-Song Xue³, Jun Deng¹

Affiliations

¹ 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.
² University of Chinese Academy of Sciences, Beijing 100049, China.
³ State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.

PMID: 33086787
DOI: 10.1021/acs.orglett.0c02865

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Biomimetics / methods*
Biosynthetic Pathways
Cycloaddition Reaction*
Dimerization
Molecular Structure
Stereoisomerism