Journal
NATURE COMMUNICATIONS
Volume 6, Issue -, Pages -Publisher
NATURE RESEARCH
DOI: 10.1038/ncomms7445
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Funding
- Ministry of Science and Technology [2013CB836900]
- National Natural Science Foundation of China [21290180, 21172235, 21222202]
- Pujiang Program [12PJ1410800]
- China Postdoctoral Science Foundation [2014M551480]
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Clostrubin is a potent antibiotic against methicillin-and vancomycin-resistant bacteria that was isolated from a strictly anaerobic bacterium Clostridium beijerinckii in 2014. This polyphenol possesses a fully substituted arene moiety on its pentacyclic scaffold, which poses a considerable challenge for chemical synthesis. Here we report the first total synthesis of clostrubin in nine steps (the longest linear sequence). A desymmetrization strategy is exploited based on the inherent structural feature of the natural product. Barton-Kellogg olefination forges the two segments together to form a tetrasubstituted alkene. A photoinduced 6p electrocyclization followed by spontaneous aromatization constructs the hexasubstituted B ring at a late stage. In total, 200 mg of clostrubin are delivered through this approach.
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