ChemInform Abstract: Diastereoselective Iodocarbocyclization Reaction of 2- or 3-Oxy-4- pentenylmalonate Derivatives.

✍ Scribed by T. INOUE; O. KITAGAWA; Y. ODA; T. TAGUCHI

• Book ID: 101844751
• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 35 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199714100

✦ Synopsis

Diastereoselective Iodocarbocyclization Reaction of 2-or 3-Oxy-4pentenylmalonate Derivatives.

-The title reaction of pentenylmalonates with an oxygenated substituent at allylic or homoallylic position proceeds with high cis-selectivity. Allylic alkyl substituents lead to lower selectivity, whereas the nature of the homoallylic substituent does not influence the strong cis-selectivity. The stereochemical outcome is discussed. The methodology is exploited for the asymmetric syntheses of intermediates of important organic molecules such as the lactone (-)-(IIa) (a precursor of cyclosarkomycin) and the lactone (VIII) (a synthetic intermediate of brefeldin A). -(INOUE, T.;