title: Enantiospecific total synthesis of (-)-bengamide E.
abstract: Total synthesis of the polyhydroxy caprolactam amide natural product, bengamide E, is accomplished starting from tartaric acid. Key reactions in the synthesis include desymmetrization of the bis(dimethylamide) unit of tartaric acid, Zn(BH(4))(2)-mediated anti-selective reduction, and a Horner-Wadsworth-Emmons olefination.
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, Sir C. V. Raman Av, Bangalore 560 012, India.
authors.forename: Prashant K
authors.initials: PK
authors.lastname: Metri
authors.forename: Raphael
authors.initials: R
authors.lastname: Schiess
authors.forename: Kavirayani R
authors.initials: KR
authors.lastname: Prasad
mesh_terms: D000475:Alkenes / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D002209:Caprolactam / Q000737:chemistry; D013237:Stereoisomerism; D013644:Tartrates / Q000737:chemistry
chemical_list: D000475:Alkenes; D000577:Amides; D001381:Azepines; D013644:Tartrates; C427481:bengamide E; D002209:Caprolactam; C029768:tartaric acid