title: Enantiospecific synthesis of (+)-N(a)-methylpericyclivine and (-)-N(a)-methylakuammidine as well as the ring-A oxygenated natural products, (+)-10-methoxy N(a)-methylpericyclivine and 10-hydroxy N(a)-methylpericyclivine.
abstract: [reaction: see text] The first enantiospecific, regiospecific total synthesis of the enantiomers of N(a)-methylpericyclivine and N(a)-methylakuammidine as well as the ring-A oxygenated natural products (+)-10-methoxy N(a)-methylpericyclivine and 10-hydroxy N(a)-methylpericyclivine was achieved. The lactones (see 19, 22, and 25) are key to the formation of the beta-axial methyl ester moiety.
authors.affiliation: Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, USA.
authors.forename: P V V
authors.initials: PV
authors.lastname: Srirama Sarma
authors.forename: James M
authors.initials: JM
authors.lastname: Cook
mesh_terms: D031051:Alstonia / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D026121:Indole Alkaloids; C514851:N(a)-methylakuammidine; C514850:N(a)-methylpericyclivine