Total synthesis of a xylo-Puromycin analog.
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.
Michel
Benoît Y
BY
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
Krishnakumar
Kollappillil S
KS
Strazewski
Peter
P
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry; D011691:Puromycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D000890:Anti-Infective Agents; C541633:N6-bis-demethylated-puromycin; D011691:Puromycin