Stereoselective allyl amine synthesis through enantioselective addition of diethylzinc and [1,3]-chirality transfer: synthesis of lentiginosine and polyoxamic acid derivative |
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Authors: | Ichikawa Yoshiyasu Ito Takashi Isobe Minoru |
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Institution: | Faculty of Science, Kochi University, Akebono-cho, Kochi 780-8520, Japan. ichikawa@cc.kochi-u.ac.jp |
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Abstract: | A new synthetic method for the preparation of allyl amines has been developed. The key steps of this method are enantioselective addition of diethylzinc and 1,3]-chirality transfer through the 3.3] sigmatropic rearrangement of allyl cyanates. Stereocontrolled syntheses of lentiginosine (1) and polyoxamic acid derivative 2 from a common intermediate 7 derived from D-tartaric acid (8), have been accomplished. |
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Keywords: | asymmetric synthesis natural products rearrangement synthesis design total synthesis |
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