Macrocyclic diterpenoids from Euphorbia hyberna L. subsp. insularis and their reaction with oxyphilic reagents.
The aerial parts of Euphorbia hyberna subsp. insularis from Sardinia contain large amounts of macrocyclic diterpenoids of the jatrophane type, while phorboids could not be isolated. Treatment of the major constituent (1a) with various acidic and oxyphilic reagents was investigated, showing the surprising reluctance of the macrocyclic system to undergo transannular reactions. Dehydration, isomerization of the exocyclic double and acyl rearrangement were, however, observed after reduction of the 9-keto group.
Appendino
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G
Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, Viale Ferrucci 33, 28100 Novara, Italy. appendino@pharm.unipmn.it
Spagliardi
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P
Ballero
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M
Seu
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D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification*; D028481:Euphorbia / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry*; D035261:Plant Components, Aerial / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry; D013055:Spectrophotometry, Infrared
D004224:Diterpenes; D010936:Plant Extracts; D010100:Oxygen