title: Stereoselective synthesis of hydroxy stilbenoids and styrenes by atom-efficient olefination with thiophthalides.
abstract: The synthesis of stilbenoids and styryl carboxylic acids is accomplished with high E-stereoselectivity by olefination of aldehydes with thiophthalides under basic conditions. The olefination is highly atom-efficient as it only loses elemental sulfur during the reaction. This olefination, in conjunction with retro Kolbe-Schmitt reaction, allows facile synthesis of E-hydroxystilbenoids with minimal employment of protecting groups. This study also discloses two important findings: formation of i) 4-methylsulfanyl isocoumarins and ii) an 2-arylindenone.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kharagpur, West Bengal, India.
authors.forename: Prithiba
authors.initials: P
authors.lastname: Mitra
authors.forename: Brateen
authors.initials: B
authors.lastname: Shome
authors.forename: Saroj Ranjan
authors.initials: SR
authors.lastname: De
authors.forename: Anindya
authors.initials: A
authors.lastname: Sarkar
authors.forename: Dipakranjan
authors.initials: D
authors.lastname: Mal
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D001572:Benzofurans / Q000737:chemistry*; D006900:Hydroxylation; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013267:Stilbenes / Q000737:chemistry*; D013343:Styrenes / Q000138:chemical synthesis*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000475:Alkenes; D001572:Benzofurans; D013267:Stilbenes; D013343:Styrenes; D013438:Sulfhydryl Compounds; C082022:phthalide