High-Yield Synthesis of 20-, 24-, and 28-Membered Macropentolide, -hexolide, and -heptolide, Respectively, from (R)- or (S)-3-hydroxybutanoic acid underYamaguchi's macrolactonization conditions
| Autor: | Peter Schnurrenberger, Dieter Seebach, Michael Przybylski, Urs Brändli |
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| Rok vydání: | 1988 |
| Předmět: |
chemistry.chemical_classification
Stereochemistry Dimer Organic Chemistry Nuclear magnetic resonance spectroscopy Biochemistry Oligomer Catalysis Inorganic Chemistry chemistry.chemical_compound Monomer chemistry Tetramer Yield (chemistry) Drug Discovery Mass spectrum Physical and Theoretical Chemistry Lactone |
| Zdroj: | Helvetica Chimica Acta. 71:155-167 |
| ISSN: | 0018-019X |
| DOI: | 10.1002/hlca.19880710119 |
| Popis: | The macrocyclic pentolide 1, hexolide 2, and heptolide 3 constitute ca. 80% of the oligomers formed in ca. 50% yield from enantiomerically pure 3-hydroxybutanoic acid under Yamaguchi's macrolactonization conditions. The FAB mass spectra of the MH+, M Na+, and MCs+ are reported (Figs. 2, 3, 5, and 6). No cyclic tetramer is detected. The 1H-NMR spectra of the cyclic oligomers, of the monomer, and of the polymer (PHB) are very similar (Fig. 4). Directed synthesis of the open-chain dimer and tetramer of 3-hydroxybutanoic acid and attempted cyclization do not lead to the isolation of the cyclic tetramer. |
| Databáze: | OpenAIRE |
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