An efficient formal synthesis of balanol is described. The thirteen-step sequence features a highly enantioselective (92% ee) ring opening of 1,4-cyclohexadiane monoepoxide with TMSN~ catalyzed by the Cr-salen complex 3. A selective Beckmann rearrangement followed by amide reduction and nitrogen fun
General synthesis of carbanucleosides via regiospecific epoxide opening by the aglycone
โ Scribed by Harald Baumgartner; Christoph Marschner; Rainer Pucher; Herfried Griengl
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- French
- Weight
- 227 KB
- Volume
- 32
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
By reaction of 1,2-anhydro-5-O-acetyl-3-O-benzyl-~-D-carbaxylofuranose 8 with the aglycone in alkaline medium followed by deprotection carbanucleosides 10 were obtained. Carbocyclic nucleosides are of relevance due to their antiviral and anticancer properties1 as well as their high bioavailability since no hydrolizeable N-acetal bond
๐ SIMILAR VOLUMES
Anilines react with epoxides in dioxane at 180ยฐC in the presence of a catalytic amount of a ruthenium catalyst along with tin(II) chloride to afford 2-substituted indoles in moderate to good yields.