title: Benzannulation for the regiodefined synthesis of 2-alkyl/aryl-1-naphthols: total synthesis of arnottin I.
abstract: The annulation of phthalides with α-alkyl/arylacrylates in the presence of LDA/LHMDS is shown to directly give alkyl/aryl-1-naphthols. The method involving a novel dealkoxycarbonylation obviates the regiochemical issues in the synthesis of polysubstituted naphthalenes, and it forms the key step in a three-step total synthesis of arnottin I, a naphthobenzopyranone natural product.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India. dmal@chem.iitkgp.ernet.in
authors.forename: Dipakranjan
authors.initials: D
authors.lastname: Mal
authors.forename: Amit Kumar
authors.initials: AK
authors.lastname: Jana
authors.forename: Prithiba
authors.initials: P
authors.lastname: Mitra
authors.forename: Ketaki
authors.initials: K
authors.lastname: Ghosh
mesh_terms: D000179:Acrylates / Q000737:chemistry; D001572:Benzofurans / Q000737:chemistry; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry*; D009284:Naphthols / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000179:Acrylates; D001572:Benzofurans; D003374:Coumarins; D009284:Naphthols; C414400:arnottin I; C082022:phthalide