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Volumn 12, Issue 32, 2006, Pages 8336-8344

An efficient access to novel enantiomerically pure steroidal δ-amino acids

Author keywords

Amino acids; Catalysis; Cross coupling; Electrocyclic reactions; Palladium; Steroids

Indexed keywords

ALCOHOLS; CATALYSIS; MICROWAVE HEATING; OPTIMIZATION; PALLADIUM; THERMODYNAMICS;

EID: 33751036480     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601076     Document Type: Article
Times cited : (13)

References (58)
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    • The bromoenol triflates were assembled from the W-substituted 4-piperidones, to the corresponding trimethylsilyl enol ethers via the α-bromopiperidinones 1a-c using very economical conditions based on trifluoromethanesulfonic acid anhydride and triethylamine : a) A. Boumendjel, J. C. Roberts, P. E. Hu, J. Org. Chem. 1996, 61, 4434-4438;
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    • note
    • The use of different amide bases such as NaHMDS or LiHMDS for an improved regioselectivity during the enolate formation in α-bromopiperidinone 1b,c led to complete decomposition of the substrates.
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    • CCDC-605599 (2b) contains the supplementary crystallographic data for compound 2b. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif/
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    • note
    • 3P in significant amounts to the catalytic cocktail led to an increased formation of side products.
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    • note
    • 3P as co-ligand also allows for a decreased loading of the precatalyst necessary for the full consumption of bromobutadienes cis-4a-c and trans-4b in Heck reactions providing higher yields for hexatrienes cis-5a-c and trans-5b at the same time.
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    • Another remarkable feature of certain 3-azasteroids is their ability to act as inhibitors of 5a-reductase which converts testosterone to 5α-dihydrotestosterone in androgen sensitive cells: a) A. J. Robinson, I. DeLucca, S. Drummond, G. A. Boswell, Tetrahedron Lett. 2003, 44, 4801-4804;
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    • note
    • 1H NOESY NMR experiments in which interactions beween the pro tons of the methyl group at C13 and the proton at C8 as well as between the proton at C7 and the proton at C8 were observed.
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    • CCDC-605600 (7b) contains the supplementary crystallographic data for compound 7b. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif/


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.