Synthesis of silyl enol and silyl dienol ethers of 20-Oxosteroids: The effect of β-substituents

Chemistry Letters

Volumn , Issue 6, 1997, Pages 529-530

  Moreno, Maria José S M ^a   Martins, Rosa Maria L M ^a   Sá E Melo, Maria Luísa ^a   Campos Neves, André S ^a  

^a UNIVERSITY OF COIMBRA   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000247046     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.529     Document Type: Article

References (17)

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2. P. Brownbridge, Synthesis, 1983, 1 and 85. J.-M. Poirier, Org. Prep. Proc. Int., 20, 317 (1988); H. B. Mekelburger and C. S. Wilcox, in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 2, p 99.
3. P. Brownbridge, Synthesis, 1983, 1 and 85. J.-M. Poirier, Org. Prep. Proc. Int., 20, 317 (1988); H. B. Mekelburger and C. S. Wilcox, in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 2, p 99.
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11. a) The β-designation refers to the position of the substituents relatively to the carbonyl group. For both substrates the stereochemistry is α.
12. 13C NMR δ 72.46 (C-17), 74.26 (C-16), 74.35 (C-3), 122.29 (C-6), 139.80 (C-5), 170.57 (MeOCO), 208.69 (C-20).
13. 3], 72.98 (C-17), 73.75 (C-16), 74.22 (C-3), 122.85 (C-6), 140.00 (C-5), 173.00 (MeOCO), 209.30 (C-20),
14. 2), 4.47 (m, 16β-H), 4.60 (m, 3α-H), 5.37 (m, 6-H).
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16. 13C NMR δ 73.86 (C-3), 121.94 (C-6), 140.15 (C-5), 144.65 (C-16), 155.21 (C-17), 170.59 (MeCOO), 196.97 (C-20).
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