title: A Maitland-Japp inspired synthesis of dihydropyran-4-ones and their stereoselective conversion to functionalised tetrahydropyran-4-ones.
abstract: The Maitland-Japp reaction has been extended to the synthesis of highly functionalised dihydropyran-4-ones. These dihydropyran-4-ones can in turn be converted stereoselectively into tetrahydropyran-4-ones with tertiary and quaternary stereocentres via the one-pot addition of hydride or carbon nucleophiles and trapping with carbon electrophiles. The utility of this method is demonstrated by providing access to the functionalised tetrahydropyran units present in a component of the Civet fragrance and the anticancer polyketide lasonolide A.
authors: Department of Chemistry, University of York, Heslington, York, North Yorkshire YO10 5DD, UK. paul.clarke@york.ac.uk.
authors: Paul A
authors: PA
authors: Clarke
authors: Philip B
authors: PB
authors: Sellars
authors: Nadiah Mad
authors: NM
authors: Nasir
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D015195:Drug Design; D018942:Macrolides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008968:Molecular Conformation; D061065:Polyketides / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D018942:Macrolides; D061065:Polyketides; D011714:Pyrans; D011753:Pyrones; D012997:Solvents; C450700:lasonolide A; D002244:Carbon