A general approach to cyathin diterpenes. Total synthesis of allocyathin B(3).
[reaction: see text] The synthesis of allocyathin B(3) from an advanced intermediate possessing the ring system and relative stereochemistry but lacking the isopropyl and hydroxymethyl groups is reported. The isopropyl group was introduced by radical cyclization of a methyl propargyl acetal of an alpha-bromo ketone, and the hydroxymethyl group was generated by Pd-catalyzed carbonylation of a vinyl triflate. The route provides functionalized intermediates that could allow access to more complex members of the cyathin family of diterpenes.
Ward
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Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK S7N 5C9 Canada.
Gai
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Qiao
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D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002855:Chromatography, Thin Layer; D004224:Diterpenes / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D010946:Plants, Medicinal / Q000737:chemistry
D000900:Anti-Bacterial Agents; D004224:Diterpenes; D007202:Indicators and Reagents; C007179:cyathins