title: The shortest synthetic route to puromycin analogues using a modified Robins approach.
abstract: We are reporting on the utility of commercial vinyl isocyanate for a practical synthetic route from adenosine to N(6)-bis-demethylpuromycin in seven steps and 65% overall yield. A clean one-pot conversion of 3'-bromo-2'-carbamoyl derivative 8 to 3'-amino-3'-deoxyadenosine derivative 10 is the main feature of this synthetic pathway. This synthesis is the shortest synthetic route toward 3'-(aminoacylamido)deoxyadenosines to date.
authors.affiliation: Laboratoire de Synthèse de Biomolécules (UMR 5246, ICBMS), Université Claude Bernard Lyon 1, 43 boulevard du 11 novembre 1918, 69622 Villeurbanne Cedex, France.
authors.forename: Kollappillil S
authors.initials: KS
authors.lastname: Krishnakumar
authors.forename: Sébastien
authors.initials: S
authors.lastname: Goudedranche
authors.forename: Denis
authors.initials: D
authors.lastname: Bouchu
authors.forename: Peter
authors.initials: P
authors.lastname: Strazewski
mesh_terms: D003839:Deoxyadenosines / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011691:Puromycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D003839:Deoxyadenosines; D007202:Indicators and Reagents; C561167:N(6)-bis-demethylpuromycin; C019247:3'-amino-3'-deoxyadenosine; D011691:Puromycin