Synthesis of 7-dehydrocholesterol through a palladium catalyzed selective homoannular conjugated diene formation

Journal of Molecular Catalysis A: Chemical

Volumn 253, Issue 1-2, 2006, Pages 119-122

  Dugas, Diane ^a   Brunel, Jean Michel ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Catalysis; Dehydrocholesterol; Elimination; Homoannular conjugated dienes; Palladium

Indexed keywords

CATALYSIS; OLEFINS; PALLADIUM; SYNTHESIS (CHEMICAL);

DEHYDROCHOLESTEROL; ELIMINATION; HOMOANNULAR CONJUGATED DIENES;

CHOLESTEROL;

EID: 33646860328     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2006.03.014     Document Type: Article

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19. 13C: δ = 12.31, 15.02, 18.99, 19.60, 23.44, 23.61, 24.34, 24.90, 27.03, 28.90, 30.29, 30.96, 32.85, 33.12, 36.71, 37.04, 38.31, 40.36, 43.24, 43.70, 49.78, 56.77, 57.00, 74.59, 120.23, 125.95, 136.12, 149.57, 157.44.
20. 13C: δ = 11.77, 15.25, 18.60, 20.84, 22.50, 22.76, 23.84, 27.89, 28.13, 35.45, 35.72, 36.10, 36.31, 39.42, 42.98, 51.42, 54.45, 56.02, 119.16, 124.13, 125.01, 127.92, 131.35, 142.58. It is noteworthy that we have not tried to isolate this derivative performing the reaction in refluxing toluene and starting from allylic carbonate 5b but it must be present since all the experimental conditions are required.
21. 13C: δ = 12.21, 16.68, 19.24, 21.51, 22.95, 23.21, 23.87, 24.27, 28.40, 32.35, 36.54, 37.40, 38.77, 39.56, 39.90, 41.15, 43.31, 46.63, 51.16, 54.89, 56.28, 70.83, 116.66, 120.00, 140.15, 141.82.
22. 13C: δ = -4.57, 11.95, 16.32, 18.20, 19.52, 21.10, 22.90, 23.15, 24.15, 25.85, 28.10, 31.12, 33.95, 36.45, 37.32, 40.21, 43.28, 46.31, 54.65, 56.32, 72.62, 109.71, 129.01, 139.20, 139.55.
23. 13C: δ = 16.01, 20.12, 26.01, 31.29, 32.58, 35.56, 37.42, 38.60, 41.06, 41.82, 44.90, 49.42, 69.71, 81.48, 119.21, 121.23, 140.14, 141.95.
24. 13C: δ = 12.06, 16.20, 18.75, 19.21, 20.32, 21.02, 23.14, 26.54, 32.22, 34.58, 37.24, 37.98, 39.54, 41.35, 43.01, 44.77, 46.88, 54.55, 55.76, 69.71, 117.65, 119.38, 131.17, 135.23, 140.70.
25. 13C: δ = 12.43, 16.67, 18.30, 20.04, 20.35, 21.49, 23.39, 28.68, 31.30, 32.38, 33.48, 37.42, 38.85, 39.48, 40.82, 41.18, 43.22, 46.65, 54.95, 56.12, 70.82, 116.69, 119.98, 132.37, 135.96, 140.19, 141.72.