ISSN:
1434-193X
Keywords:
Functionalized hydroazulenes
;
Wittig reaction
;
Selective additions
;
Resolution
;
X-ray analyses
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Treatment of the bridged oxepine (±)-1 with a large excess of powdered sodium methoxide in Et2O or with triphenylphosphonium methylide leads to the functionalized hydroazulenes (±)-2 (69%) and (±)-3 (81%). Regioselective and stereoselective cyclopropanation of (±)-2 leads to the dibromocyclopropane derivative (±)-4. Epoxidation gives the epoxides (±)-5 and (±)-6. The resolution of the hydro-azulenone (±)-2 is achieved by fractional crystallization of the quinine salt (-)-8 of the corresponding mono acid (±)-7. The absolute configuration of (+)-7 is established by X-ray analysis of the quinine salt (-)-8.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
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