Stereoselective synthesis of enantiopure analogues of (-)-cephalotaxine
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作者:
Berhal, Farouk
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Univ Paris 05, CNRS, UMR 8638, Fac Sci Pharmaceut & Biol, F-75270 Paris 06, FranceUniv Paris 05, CNRS, UMR 8638, Fac Sci Pharmaceut & Biol, F-75270 Paris 06, France
Berhal, Farouk
[1
]
Perard-Viret, Joelle
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Univ Paris 05, CNRS, UMR 8638, Fac Sci Pharmaceut & Biol, F-75270 Paris 06, FranceUniv Paris 05, CNRS, UMR 8638, Fac Sci Pharmaceut & Biol, F-75270 Paris 06, France
Perard-Viret, Joelle
[1
]
Royer, Jacques
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Univ Paris 05, CNRS, UMR 8638, Fac Sci Pharmaceut & Biol, F-75270 Paris 06, FranceUniv Paris 05, CNRS, UMR 8638, Fac Sci Pharmaceut & Biol, F-75270 Paris 06, France
Royer, Jacques
[1
]
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[1] Univ Paris 05, CNRS, UMR 8638, Fac Sci Pharmaceut & Biol, F-75270 Paris 06, France
The asymmetric total synthesis of three analogues of (-)-cephalotaxine with structural modification of the aromatic ring was achieved in 16 steps and acceptable overall yields. The procedure used was quite similar to that reported by our group for the total synthesis of (-)-cephalotaxine in 2004. The enantio-pure spiranic compound 4 is a common intermediate on which various aromatic groups can be introduced. Unexpected and interesting different chemical behaviors were observed during these syntheses. (C) 2010 Elsevier Ltd. All rights reserved.