title: Total synthesis of (-)-himgaline.
abstract: The first total synthesis of (-)-himgaline and a highly enantioselective synthesis of its congener (-)-GB 13 are described. Decarboxylative aza-Michael reaction of the hexacyclic lactone precursor under acidic conditions, followed by basic workup, yielded (-)-GB 13 in 80% yield. Cyclization of (-)-GB 13 to oxohimgaline under acidic conditions, followed by internally coordinated sodium triacetoxyborohydride reduction, gave (-)-himgaline as the exclusive product.
authors.affiliation: Schering-Plough Research Institute, 2015 Galloping Hill Road, Kenilworth, NJ 07033, USA.
authors.forename: Unmesh
authors.initials: U
authors.lastname: Shah
authors.forename: Samuel
authors.initials: S
authors.lastname: Chackalamannil
authors.forename: Ashit K
authors.initials: AK
authors.lastname: Ganguly
authors.forename: Mariappan
authors.initials: M
authors.lastname: Chelliah
authors.forename: Sergei
authors.initials: S
authors.lastname: Kolotuchin
authors.forename: Alexei
authors.initials: A
authors.lastname: Buevich
authors.forename: Andrew
authors.initials: A
authors.lastname: McPhail
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis; D018360:Crystallography, X-Ray; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D024301:Plant Bark / Q000737:chemistry; D014197:Trees / Q000737:chemistry
chemical_list: D001643:Bridged Bicyclo Compounds; C518378:Galbulimima alkaloid 13; D006571:Heterocyclic Compounds; C518376:himgaline