Synthetic studies towards lagunamide C: Polyketide assembly investigations
| Autor: | Ryan J. Rafferty, Chelsea Weese, Salvador Valdez, Anthony Fatino, Alberto Jiménez-Somarribas |
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| Rok vydání: | 2018 |
| Předmět: |
Depsipeptide
Natural product 010405 organic chemistry Chemistry Cyclopropanation Stereochemistry Organic Chemistry Ring (chemistry) 01 natural sciences Biochemistry Pentapeptide repeat 0104 chemical sciences Stereocenter 010404 medicinal & biomolecular chemistry Polyketide chemistry.chemical_compound Aldol reaction Drug Discovery |
| Zdroj: | Tetrahedron Letters. 59:624-627 |
| ISSN: | 0040-4039 |
| Popis: | Lagunamide C is a depsipeptide natural product with low nM cytotoxicity towards numerous cancer cell lines. Synthetically, it is disconnected to a pentapeptide backbone and polyketide unit that possesses four stereogenic centers, of which two of centers are in question (C38 & 40). Our model system highlights a high-selective aldol addition via a Crimmin’s auxiliary setting the C40 ester linkage, and a non-facially selective cyclopropanation with subsequent ring opening for the installation of the C38 methyl center. |
| Databáze: | OpenAIRE |
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