title: Synthesis of Vitamin K and Related Naphthoquinones via Demethoxycarbonylative Annulations and a Retro-Wittig Rearrangement.
abstract: Anionic annulations of 3-nucleofugal phthalides with α-alkyl(aryl)acrylates involving a demethoxycarbonylation provide a succinct synthesis of vitamin K and related naphthoquinones. Also reported is a new cascade reaction stemming from a Cope-retro-Wittig rearrangement. This cascade leads to direct formation of 1-hydroxy-4-prenyloxynaphthalene-2-carboxylates from the corresponding α-prenyl acrylate acceptors.
authors.affiliation: Department of Chemistry, Indian Institute of Technology , Kharagpur 721302, India.
authors.forename: Dipakranjan
authors.initials: D
authors.lastname: Mal
authors.affiliation: Department of Chemistry, Indian Institute of Technology , Kharagpur 721302, India.
authors.forename: Ketaki
authors.initials: K
authors.lastname: Ghosh
authors.affiliation: Department of Chemistry, Indian Institute of Technology , Kharagpur 721302, India.
authors.forename: Supriti
authors.initials: S
authors.lastname: Jana
mesh_terms: D000179:Acrylates / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014812:Vitamin K / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000179:Acrylates; D002264:Carboxylic Acids; D009285:Naphthoquinones; D014812:Vitamin K; C036658:acrylic acid