Synthesis of the cyclobutylfuran sector of providencin via zirconium-mediated oxygen abstraction from a furanoside.
A portion of the macrocyclic cembrenoid diterpene providencin possessing conjoined cyclobutane and furancarboxylate units was synthesized from D-glucose using deoxygenative ring contraction methodology to construct the tetrasubstituted cyclobutane and a Knoevenagel condensation of glyceraldehyde to fabricate the trisubstituted furan.
White
James D
JD
Department of Chemistry, Oregon State University, Corvallis, Oregon 97331-4003, USA. james.white@oregonstate.edu
Jana
Somnath
S
D002384:Catalysis; D003503:Cyclobutanes / Q000138:chemical synthesis* / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry; D015040:Zirconium / Q000737:chemistry*
D003503:Cyclobutanes; D004224:Diterpenes; D005663:Furans; D006027:Glycosides; C478991:providencin; D015040:Zirconium; D010100:Oxygen