Toward the Synthesis of Thapsigargin: Enantioselective Synthesis of 7,11-Dihydroxyguaianolides
| Autor: | Guillermo M. Massanet, Zacarías D. Jorge, F. Javier Moreno-Dorado, Francisco M. Guerra, Francisco L. Manzano |
|---|---|
| Rok vydání: | 2006 |
| Předmět: |
chemistry.chemical_classification
Thapsigargin Ketone Molecular Structure Stereochemistry Organic Chemistry Enantioselective synthesis Regioselectivity Stereoisomerism Biochemistry Catalysis Sesquiterpenes Guaiane chemistry.chemical_compound chemistry Molecule Physical and Theoretical Chemistry Thapsia |
| Zdroj: | Organic Letters. 8:2879-2882 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol061024z |
| Popis: | [reaction: see text] The enantioselective synthesis of a 7,11-dihydroxyguaianolide bearing the stereochemistry present in thapsigargin, a potent and selective inhibitor of the Ca(2+) SERCA-ATPase pumps, is described. Starting from (+)-dihydrocarvone, the synthesis presents two key steps. The first one involves the photochemical rearrangement of a gamma,delta-unsaturated ketone eudesmane into the corresponding guaiane. The second step consists of the regioselective oxidation of an unprotected tetrahydroxylated ketone to provide a dihydroxylactone with the required stereochemistry. |
| Databáze: | OpenAIRE |
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