The first enantioselective synthesis of imino-deoxydigitoxose and protected imino-digitoxose by using l-threonine aldolase-catalyzed aldol condensation
| Autor: | Swapnil Surendra Mohile, Tetsuya Kajimoto, Teppei Otsuda, Toshihiro Nishiyama, Manabu Node, Noboru Hayama, Minoru Ozeki |
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| Rok vydání: | 2009 |
| Předmět: |
biology
Stereochemistry Organic Chemistry Aldolase A Enantioselective synthesis Catalysis Inorganic Chemistry chemistry.chemical_compound chemistry Nucleophile biology.protein Organic chemistry Hemiacetal heterocyclic compounds Acid hydrolysis Aldol condensation Piperidine Physical and Theoretical Chemistry Threonine |
| Zdroj: | Tetrahedron: Asymmetry. 20:230-234 |
| ISSN: | 0957-4166 |
| DOI: | 10.1016/j.tetasy.2008.12.029 |
| Popis: | The first enantioselective synthesis of protected imino-digitoxose (−)- 16 was attained starting with a synthetic intermediate of polyoxin C prepared by the l -threonine aldolase-catalyzed aldol condensation of (2 S ,3 S )-2,3- O- isopropyriden-4-penten-1-al 8 and glycine. The strategy took advantage of an intramolecular nucleophilic attack by a Cbz-protected amino group on the hemiacetal carbon, a side reaction in the synthesis of natural products, for the formation of the piperidine ring of the imino-sugar. Imino-deoxydigitoxose (+)- 18 was also synthesized from (−)- 16 by reduction and acid hydrolysis. |
| Databáze: | OpenAIRE |
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