Synthetic studies toward sordarin: building blocks for the terpenoid core and for analogues thereof.
Avenues to bi- and tricyclic building blocks for the elaboration of sordaricin and its analogues are described. The target molecules were obtained through inter- and intramolecular Diels-Alder reactions of a number of previously unknown cyclopentadienes. Unusual properties of 3-cyanoenones and 1-cyanocyclopentadienes have been unveiled and circumvented.
Schulé
Arnaud
A
Laboratoire de Synthèse et Méthodologie Organiques, CNRS UMR 5181, Université Claude Bernard Lyon 1 and Ecole Supérieure de Chimie, Physique, Electronique de Lyon, 43, Bd. du 11 Novembre 1918, 69622 Villeurbanne, France.
Liang
Huan
H
Vors
Jean-Pierre
JP
Ciufolini
Marco A
MA
D002264:Carboxylic Acids / Q000737:chemistry; D003517:Cyclopentanes / Q000737:chemistry; D007192:Indenes / Q000138:chemical synthesis* / Q000737:chemistry; D009570:Nitriles / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D011500:Protein Synthesis Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry*
D002264:Carboxylic Acids; D003517:Cyclopentanes; D007192:Indenes; D009570:Nitriles; D011500:Protein Synthesis Inhibitors; D013729:Terpenes; C003329:sordarin; D010100:Oxygen