title: Enantioselective synthesis of δ-/γ-alkoxy-β-hydroxy-α-alkyl-substituted Weinreb amides via DKR-ATH: application to the synthesis of advanced intermediate of (-)-brevisamide.
abstract: A method of preparing stereodefined δ-/γ-alkoxy-β-hydroxy-α-alkyl-substituted Weinreb amides containing two successive hydroxyl-alkyl stereocenters has been developed. Further, this strategy coupled with organo-catalyzed asymmetric epoxidation culminates in the synthesis of a critical intermediate of (-)-brevisamide and its diastereomers.
authors.affiliation: Organic & Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 607, India. gkswamy_iict@yahoo.co.in.
authors.forename: Gullapalli
authors.initials: G
authors.lastname: Kumaraswamy
authors.forename: Akula
authors.initials: A
authors.lastname: Narayana Murthy
authors.forename: Vykunthapu
authors.initials: V
authors.lastname: Narayanarao
authors.forename: Sahithya Phani Babu
authors.initials: SP
authors.lastname: Vemulapalli
authors.forename: Jagadeesh
authors.initials: J
authors.lastname: Bharatam
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D000577:Amides / Q000138:chemical synthesis*; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry; D006900:Hydroxylation; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D000095702:Polyether Toxins
chemical_list: D000438:Alcohols; D000470:Alkaloids; D000577:Amides; D004852:Epoxy Compounds; D011714:Pyrans; C059688:alkoxyl radical; C532303:brevisamide; D000095702:Polyether Toxins