Studies toward the synthesis of an oxazole-based analog of (−)-zampanolide
| Autor: | Cindy Klaus, Christian P. Bold, Karl-Heinz Altmann, J. Fernando Díaz, Jasmine Schürmann, Rafael Lombardi, Bernhard Pfeiffer, Daniel Lucena-Agell |
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| Přispěvatelé: | Swiss National Science Foundation, Ministerio de Ciencia e Innovación (España), Instituto de Salud Carlos III, European Commission, Klaus, Cindy [0000-0001-5977-1158], Pfeiffer, Bernhard [0000-0002-6209-0705], Lucena-Agell, Daniel [0000-0001-7198-2900], Díaz, José Fernando [0000-0003-2743-3319], Altmann, Karl-Heinz [0000-0002-0747-9734], Klaus, Cindy, Pfeiffer, Bernhard, Lucena-Agell, Daniel, Díaz, José Fernando, Altmann, Karl-Heinz |
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
Zampanolide Double bond 010405 organic chemistry Stereochemistry Organic Chemistry Alcohol Tetrahydropyran 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry 0104 chemical sciences 3. Good health chemistry.chemical_compound chemistry Physical and Theoretical Chemistry Oxazole |
| Zdroj: | Digital.CSIC. Repositorio Institucional del CSIC instname Organic Letters, 23 (6) |
| Popis: | 5 p.-2 fig.-4 schem.-1 graph. abst. Studies are described toward the synthesis of an oxazole-based analog of (−)-zampanolide (2). Construction of (−)-dactylolide analog 22 was achieved via alcohol 5 and acid 4 through esterification and Horner–Wadsworth–Emmons (HWE)-based macrocyclization; however, attempts to attach (Z,E)-sorbamide to 22 proved unsuccessful. The C(8)–C(9) double bond of the macrocycle was prone to migration into conjugation with the oxazole ring, which may generally limit the usefulness of zampanolide analogs with aromatic moieties as tetrahydropyran replacements. We gratefully acknowledge financial support by the Swiss National Science Foundation (Projects 200021_149253 and 200020_175744 (K.H.A.)). Funding was also obtained from Ministerio de Ciencia e Innovación PID2019-104545RB-I00 and Fondo de Investigaciones Sanitarias COV20/01007 (J.F.D.) and H2020-MSCA-ITN-2019 860070 TUBINTRAIN (J.F.D.). |
| Databáze: | OpenAIRE |
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