Palladium-assisted route to carbocyclic nucleosides: A formal synthesis of (±)-aristeromycin
✍ Scribed by Donald R Deardorff; Michael J Shulman; James E Sheppeck II
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 266 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
## Abstract (+)‐(1__R__,4__R__)‐Bicyclo[2.2.1]hept‐5‐en‐2‐one (7) was prepared in 78.5% yield by oxidative degradation of (+)‐(1__R__)‐__endo__‐bicyclo[2.2.1]hept‐5‐ene‐2‐carboxylic acid (4) by using an improved procedure for the oxidation of the dianion of 4 with dioxygen. Dihydroxylation of 7 wit
(土)-trans-1-[2-(Hydroxymethyl)cyclopentylmethyl]uracil (1) was prepared in two steps and \(56 \%\) yield from 2-hydroxymethylcyclopentylmethylamine (7) and 3-methoxy-2-propenoylisocyanate (6). Isocyanate 6 was prepared from methyl 3-methoxy-2-propenoate in four steps and \(38 \%\) overall yield.
A Slightly Shorter Route to Carbocyclic Nucleosides. Synthesis of (±)-trans-1-[2-(Hydroxymethyl)cyclopentylmethyl]uracil. -Nucleoside analogue (VIII) is synthesized by constructing the uracil base around the amino alcohol precursor (VI). Isocyanate (V) is equally suitable for formation of the base