title: Biomimetic Total Synthesis of the Pentacyclic Amaryllidaceae Alkaloid Derivative Gracilamine.
abstract: The illustrated azomethine ylide, produced through a Schiff base condensation of the corresponding aldehyde-containing C3a-arylhexahydroindole with ethyl l-leucinate, engages in a stereoselective intramolecular cycloaddition reaction to give adduct 23 that has been elaborated, over eight steps, into the racemic modification of the alkaloid derivative gracilamine (1). The formation of this ylide and its conversion into isomer 23 mimics the proposed biogenesis of the pentacyclic framework of compound 1.
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors.forename: Nadia Yuqian
authors.initials: NY
authors.lastname: Gao
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors.forename: Martin G
authors.identifier: 0000-0002-0582-475X
authors.initials: MG
authors.lastname: Banwell
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors.forename: Anthony C
authors.initials: AC
authors.lastname: Willis
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis*; D001391:Azo Compounds / Q000737:chemistry; D040761:Biomimetic Materials / Q000138:chemical synthesis*; D002384:Catalysis; D061565:Cycloaddition Reaction; D006801:Humans; D007211:Indoles / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry
chemical_list: D000447:Aldehydes; D047151:Amaryllidaceae Alkaloids; D001391:Azo Compounds; D007211:Indoles; D013882:Thiosemicarbazones; C512188:azomethine; C578306:gracilamine; D010165:Palladium; C030374:indole