Radical oxidative cyclization of spiroacetals to bis-spiroacetals: an overview.
The use of iodobenzene diacetate and iodine under photolytic conditions provides and efficient method for the oxidative cyclization of spiroacetals bearing an hydroxyalkyl side chain to bis-spiroacetals. An overview is provided of the use of this reaction for the synthesis of several bis-spiroacetal containing natural products such as the polyether antibiotics salinomycin and CP44,161 and the shellfish toxins, the spirolides.
Brimble
Margaret A
MA
Department of Chemistry, University of Auckland, 23 Symonds St., Auckland, New Zealand. m.brimble@auckland.ac.nz
D000080:Acetals / Q000737:chemistry*; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D004987:Ethers / Q000138:chemical synthesis / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry; D013141:Spiro Compounds / Q000737:chemistry*; D000095662:Polyether Polyketides
D000080:Acetals; D001952:Bridged-Ring Compounds; D004987:Ethers; D011714:Pyrans; D013141:Spiro Compounds; C425408:CP44,161; C010327:salinomycin; D000095662:Polyether Polyketides