Total Synthesis of (−)-Exiguolide
| Autor: | Cyril Cook, Xavier Guinchard, Frédéric Liron, Emmanuel Roulland |
|---|---|
| Přispěvatelé: | Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC) |
| Rok vydání: | 2010 |
| Předmět: |
Double bond
Stereochemistry Convergent synthesis Marine Biology [SDV.BC]Life Sciences [q-bio]/Cellular Biology 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry Catalysis Ruthenium Stereocenter chemistry.chemical_compound Organometallic Compounds Animals Physical and Theoretical Chemistry chemistry.chemical_classification Biological Products Molecular Structure 010405 organic chemistry Organic Chemistry Total synthesis Stereoisomerism Tetrahydropyran Porifera 0104 chemical sciences chemistry Stereoselectivity Macrolides Enantiomer |
| Zdroj: | Organic Letters Organic Letters, American Chemical Society, 2010, 12 (4), pp.744-7. ⟨10.1021/ol902829e⟩ |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | International audience; The first total synthesis of the naturally occurring enantiomer of exiguolide ((-)-1) has been completed. This very convergent synthesis features the following as main steps: (i) a Trost's ruthenium-catalyzed ene-yne cross-coupling reaction (this complex transformation allows the challenging control of the C5-C28 double bond geometry along with the stereoselective construction of the tetrahydropyran ring A) and (ii) a very efficient one-pot, two-step stereoselective conjugated allylic alcohol substitution that allowed the control of the C15 stereogenic center. |
| Databáze: | OpenAIRE |
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