title: Total synthesis of a xylo-Puromycin analog.
abstract: N(6)-bis-demethylated xylo-Puromycin analog 2 was synthesized in 56% over 6 steps from adenosine 3, involving a Mattocks bromo acetylation, a regio- and stereo-selective ribo-epoxide ring opening with sodium azide and an efficient Staudinger-Vilarrasa coupling reaction for which the conditions have been optimized.
authors.affiliation: Laboratoire de Synthèse de Biomolécules, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (UMR 5246), Université Claude Bernard Lyon 1, 69622, Villeurbanne, France. benoit.michel@yahoo.fr
authors.forename: Benoît Y
authors.initials: BY
authors.lastname: Michel
authors.forename: Kollappillil S
authors.initials: KS
authors.lastname: Krishnakumar
authors.forename: Peter
authors.initials: P
authors.lastname: Strazewski
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry; D011691:Puromycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000890:Anti-Infective Agents; C541633:N6-bis-demethylated-puromycin; D011691:Puromycin