Total synthesis of palytoxin carboxylic acid and palytoxin amide
| Autor: | Robert W. Armstrong, L. D. Hawkins, Haolun Jin, Hiromichi Fujioka, Sung Ho Kang, W. J. Christ, Seung Hoon Cheon, Jean Marie Beau, Won Hun Ham |
|---|---|
| Rok vydání: | 1989 |
| Předmět: |
chemistry.chemical_classification
animal structures Aqueous solution medicine.drug_class Carboxylic acid Total synthesis Carboxamide General Chemistry Biochemistry Catalysis Hydrolysis chemistry.chemical_compound Colloid and Surface Chemistry chemistry Palytoxin Amide Yield (chemistry) medicine Organic chemistry |
| Zdroj: | Journal of the American Chemical Society. 111:7530-7533 |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/ja00201a038 |
| Popis: | The total synthesis of palytoxin carboxylic acid and palytoxin amide was achieved from the fully protected palytoxin carboxylic acid. The fully protected palytoxin carboxylic acid 1 contains eight different and 42 total protecting groups. All these protecting groups were successfully removed in five synthetic operations, i.e., (1) DDQ treatment, (2) aqueous HClO 4 hydrolysis, (3) aqueous LiOH hydrolysis, (4)(n-Bu) 4 NF treatment, and (5) aqueous AcOH hydrolysis. The completely deprotected palytoxin carboxylic acid was isolated in approximately 35% overall yield and identified with the authentic sample. An efficient method to convert palytoxin carboxylic acid 2 into palytoxin amide 3 was developed |
| Databáze: | OpenAIRE |
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