title: A concise synthesis of siphonodictidine.
abstract: Siphonodictidine (1) has been synthesized for the first time in a concise and regiocontrolled manner by using 2-(tert-butyldimethylsiloxy)-3-methylfuran (6) as the crucial building block. The silver trifluoroacetate-induced alkylation of 6 with omega-bromogeranyl acetate 7 gave the key gamma-lactone intermediate 8, which on subsequent reduction, conversion of the hydroxyl into the amino group, and amidination afforded siphonodictidine (1) in an overall yield of 25.7% from 6.
authors.affiliation: Department of Organic Chemistry, University of Geneva, 30 quai Ernest-Ansermet, 1211 Geneva 4, Switzerland. Charles.Jefford@chiorg.unige.ch
authors.forename: Charles W
authors.initials: CW
authors.lastname: Jefford
authors.forename: Jean-Claude
authors.initials: JC
authors.lastname: Rossier
authors.forename: John
authors.initials: J
authors.lastname: Boukouvalas
authors.forename: Adam W
authors.initials: AW
authors.lastname: Sledeski
authors.forename: Ping-Zhong
authors.initials: PZ
authors.lastname: Huang
mesh_terms: D000478:Alkylation; D000818:Animals; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D012717:Sesquiterpenes / Q000032:analysis / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: C492415:2-(tert-butyldimethylsiloxy)-3-methylfuran; D005663:Furans; D007202:Indicators and Reagents; D017646:Organosilicon Compounds; D012717:Sesquiterpenes; C492414:siphonodictidine