Synthesis of a 4,5-epoxy-2-cyclohexen-1-one derivative via epoxide ring opening, 1,3-carbonyl transposition and epoxide ring regeneration: a synthetic study on a scyphostatin analogue
| Autor: | Ryukichi Takagi, Katsuo Ohkata, Kengo Tojo, Masato Iwata |
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| Rok vydání: | 2005 |
| Předmět: |
Spectrometry
Mass Electrospray Ionization Magnetic Resonance Spectroscopy Chemistry Stereochemistry Wharton reaction Organic Chemistry Epoxide Halogenation Ring (chemistry) Biochemistry Amides Adduct chemistry.chemical_compound Cyclohexanes Pyrones Spectroscopy Fourier Transform Infrared Moiety Epoxy Compounds Stereoselectivity Physical and Theoretical Chemistry Derivative (chemistry) |
| Zdroj: | Organicbiomolecular chemistry. 3(10) |
| ISSN: | 1477-0520 |
| Popis: | A 6-alkyl-4,5-epoxy-6-hydroxy-2-cyclohexen-1-one derivative, a model compound for the hydrophilic moiety of scyphostatin, was stereoselectively synthesized from the Diels–Alder adduct. The key steps were the reductive cleavage of the 4,5-epoxide ring of the epoxidated adduct, the 1,3-carbonyl transposition of the 3-carbonyl group to the C1 position by a Wharton reaction and stereoselective bromination to provide a trans bromohydrin derivative, a precursor to the desired compound. Desilylation of the bromohydrin derivative with TBAF directly gave the target compound. |
| Databáze: | OpenAIRE |
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