title: Nazarov cyclization of divinyl and arylvinyl epoxides: application in the synthesis of resveratrol-based natural products.
abstract: New variation in the Nazarov cyclization has been developed by preparing divinyl and arylvinyl epoxides as pentadienyl cation precursors for the first time. Highly substituted cyclopentadienes, hydrindienes, and indenes were synthesized to demonstrate the compatibility of this reaction with substrates bearing a variety of substitutions and having different types of epoxides. Application of this method in the synthesis of resveratrol-based natural products was also demonstrated.
authors.affiliation: Division of CPC (Organic Chemistry-II), CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500007 (India). gsudhakar@iict.res.in.
authors.forename: Gangarajula
authors.initials: G
authors.lastname: Sudhakar
authors.forename: Kovela
authors.initials: K
authors.lastname: Satish
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D000077185:Resveratrol; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001688:Biological Products; D003517:Cyclopentanes; D004852:Epoxy Compounds; D013267:Stilbenes; D000077185:Resveratrol
keywords: Nazarov cyclization; cyclopentadienes; dienyl epoxides; natural products; pentadienyl cation