title: Stereocontrol by quaternary centres: a stereoselective synthesis of (-)-luminacin D.
abstract: Very high diastereoselectivity can be achieved by 1,3-chelation-controlled allylation of aldehydes that possess a non-chelating α-ether substituent, even if the α-position is a quaternary centre and/or a spiro-epoxide. This reaction was used as a key step in an enantioselective synthesis of the angiogenesis inhibitor luminacin D.
authors: Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ (UK).
authors: Nathan
authors: N
authors: Bartlett
authors: Leona
authors: L
authors: Gross
authors: Florent
authors: F
authors: Péron
authors: Daniel J
authors: DJ
authors: Asby
authors: Matthew D
authors: MD
authors: Selby
authors: Ali
authors: A
authors: Tavassoli
authors: Bruno
authors: B
authors: Linclau
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry*; D002384:Catalysis; D002614:Chelating Agents / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D004986:Ether / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001547:Benzaldehydes; D002614:Chelating Agents; D004852:Epoxy Compounds; D013141:Spiro Compounds; C413565:luminacin D; D004986:Ether
keywords: allylation; chelation; enantioselectivity; luminacin D; stereoinduction