Synthesis of the complete carbocyclic skeleton of vinigrol

Organic Letters

Volumn 5, Issue 7, 2003, Pages 1139-1142

  Gentric, Lionel ^a   Hanna, Issam ^a   Ricard, Louis ^b  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

^b LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENOID; UNCLASSIFIED DRUG; VINIGROL; DITERPENE;

ARTICLE; CHROMATOGRAPHY; DRUG SYNTHESIS; ISOMER; NUCLEAR OVERHAUSER EFFECT; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY; CHEMICAL STRUCTURE; CHEMISTRY; FUNGUS; STEREOISOMERISM; SYNTHESIS;

DITERPENES; FUNGI; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 0042743752     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034217k     Document Type: Article

References (40)

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38. In this reaction NaH (80% dispersion in mineral oil) was used without washing, and the solvent was not degassed. In contrast, exposure of 23 to oil-free KH in carefully degassed THF at reflux for more than 3 h led to a mixture of products from which 24 was isolated in modest yield.
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40. Initial attempts to carry out the epoxidation of 29 failed: the resulting epoxide rapidly underwent an intramolecular ring opening by the hydroxyl group producing the corresponding cyclic ether.