## Abstract [4‐^13^C]‐porphobilinogen 1a, [3‐^13^C]‐porphobilinogen 1b and [11‐^13^C]‐porphobilinogen 1c are prepared from [1‐^13^C]‐3‐(tetrahydropyran‐2′‐yloxy)‐propionaldehyde 2a, methyl [4‐^13^C]‐4‐nitrobutyrate 3b and [1‐^13^C]‐isocyanoacetonitrile 5c, respectively. The building blocks 2, 3 and
A synthesis of porphobilinogen-11-13C
✍ Scribed by Graciela Buldain; Aldonia Valasinas
- Publisher
- John Wiley and Sons
- Year
- 1982
- Tongue
- French
- Weight
- 214 KB
- Volume
- 19
- Category
- Article
- ISSN
- 0022-2135
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
Porphobilinogen‐11‐^13^C was prepared by using benzyl 3‐(β‐methoxycarbonylethyl)‐4‐ (methoxycarbonylmethyl)‐2‐pyrrolecarboxylate as a starting material. A Vilsmeier‐Haak formylation with N,N′‐dimethylform‐^13^C‐amide gave the 2‐formylpyrrole, which was transformed into its oxime, and the latter was hydrogenated to the hydrochioride of 5‐carboxyporphobilinogen dimethyl ester. The hydrochloride cyclized to 5‐carboxyporphobilinogen lactam at pH 9, and the latter was first decarboxylated and then saponified to give the title compound.
📜 SIMILAR VOLUMES
## Abstract A “one pot” reduction of ethyl [1,2‐^13^C~2~]bromoacetate with diisobutylaluminium hydride in dichloromethane, followed by reaction with triphenylphosphine, then triethylamine, yields [1,2‐^13^C~2~]formylmethylenetriphenylphosphorane. Consecutive Wittig reactions of [1,2‐^13^C~2~] formy