title: Formation of highly substituted tetrahydropyranones: application to the total synthesis of cyanolide A.
abstract: A new tetrahydropyranone synthesis has been developed that leads to cis-2,6-disubstituted 3,3-dimethyltetrahydropyran-4-one rings by condensation of an aldehyde and a hydroxy silyl enol ether. The reaction works with a variety of aldehydes to produce the tetrahydropyranone products in moderate to high yields. This new method was applied to the enantioselective synthesis of cyanolide A and its aglycone.
authors: Department of Chemistry, 1102 Natural Sciences II, University of California-Irvine, Irvine, California 92697, USA.
authors: Gidget C
authors: GC
authors: Tay
authors: Michael R
authors: MR
authors: Gesinski
authors: Scott D
authors: SD
authors: Rychnovsky
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D004987:Ethers / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000447:Aldehydes; D004987:Ethers; D018942:Macrolides; D011753:Pyrones; C548188:cyanolide A