A novel route to preussomerins via 2-arylacetal anions.
[reaction--see text] Dimerization of salicylaldehydes provided 6H,12H-6,12-epoxydibenzo[b, f][1,5]dioxocins in multigram quantities. Deprotonation-allylation of the benzylic acetals followed by further functionalization of the diallyl derivative and double Friedel-Crafts cyclization gave a novel preussomerin analogue which possessed the full carbon skeleton of the natural products.
Ragot
J P
JP
Department of Chemistry, University of York, Heslington, York YO10 5DD, U.K.
Prime
M E
ME
Archibald
S J
SJ
Taylor
R J
RJ
D000080:Acetals / Q000737:chemistry; D019883:Alkyl and Aryl Transferases / Q000037:antagonists & inhibitors; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry; D001203:Ascomycota / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry; D005656:Fungal Proteins / Q000138:chemical synthesis / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry*
D000080:Acetals; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D004791:Enzyme Inhibitors; D004852:Epoxy Compounds; D005656:Fungal Proteins; D006576:Heterocyclic Compounds, 4 or More Rings; D013141:Spiro Compounds; D019883:Alkyl and Aryl Transferases; C064911:p21(ras) farnesyl-protein transferase