title: Total synthesis of enantiopure 1,3-dimethylpyranonaphthoquinones including ventiloquinones E, G, L and eleutherin.
abstract: A new synthetic approach to enantiopure pyranonaphthoquinones is described. (S)-Mellein 10, prepared in 6 steps from (S)-propylene oxide 16, is converted stereospecifically to the (1R,3S)-dimethylpyran 15. The pyran 15 is then converted to the benzoquinone 14, which undergoes regiospecific Diels-Alder reactions with a variety of oxygenated butadienes to give pyranonaphthoquinones including ventiloquinones E, G, L, eleutherin and ent-deoxyquinone A.
authors.affiliation: School of Chemistry, University of Melbourne, Victoria, Australia3010.
authors.forename: Leonie M
authors.initials: LM
authors.lastname: Tewierik
authors.forename: Christian
authors.initials: C
authors.lastname: Dimitriadis
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Donner
authors.forename: Melvyn
authors.initials: M
authors.lastname: Gill
authors.forename: Brendan
authors.initials: B
authors.lastname: Willems
mesh_terms: D001578:Benzopyrans / Q000737:chemistry; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*; D011809:Quinones / Q000737:chemistry
chemical_list: D001578:Benzopyrans; D007202:Indicators and Reagents; D009285:Naphthoquinones; D011714:Pyrans; D011809:Quinones; C415044:eleutherin