Synthesis of Dihydroplakortin, 6-epi-Dihydroplakortin, and Their C10-Desethyl Analogues
| Autor: | Orazio Taglialatela-Scafati, Salvatore Sanna Coccone, Ettore Novellino, Giuseppe Campiani, Francesc Marti, Emanuele Gabellieri, Stefania Butini, Sandra Gemma |
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| Přispěvatelé: | Gemma, S., Gabellieri, E., Sanna Coccone, S., Marti, F., TAGLIALATELA SCAFATI, Orazio, Novellino, Ettore, Campiani, G., Butini, S. |
| Jazyk: | angličtina |
| Rok vydání: | 2010 |
| Předmět: |
chemistry.chemical_classification
Aldehydes Chiral auxiliary antimalarial Molecular Structure synthesis Stereochemistry Organic Chemistry Diol Stereoisomerism Aldehyde Chemical synthesis Peroxides Stereocenter chemistry.chemical_compound chemistry Cyclization Wittig reaction Combinatorial Chemistry Techniques Epoxy Compounds Marine Toxins Epimer Nuclear Magnetic Resonance Biomolecular Marine toxin endoperoxide |
| Popis: | The first synthesis of the marine endoperoxide 9,10-dihydroplakortin, of its C10-desethyl analogue, and of their corresponding C6 epimers is described. Stereogenic centers at C4 and at the lateral chain have been stereoselectively synthesized through Evans' chiral auxiliary chemistry. Moreover, the reported synthesis features a one-pot three-step hydroperoxysilylation/cyclization reaction for the construction of the endoperoxide ring system. Homologation of the aldehyde resulting from diol cleavage through a Wittig-based strategy gave access to the ester-containing lateral chain at C3. |
| Databáze: | OpenAIRE |
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