A stereoselective synthesis of the C3-C12 subunit of the tumor growth inhibitors laulimalide is disclosed. The key steps of the synthesis include asymmetric alkylation using Oppolzer's protocol and an asymmetric hetero-Diels-Alder reaction using Jacobsen's catalyst. Substrate controlled diastereoselective Luche reduction followed by Ferrier type reactions are other key steps. (C) 2013 Elsevier Ltd. All rights reserved.
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Toyama Med & Pharmaceut Univ, Fac Pharmaceut Sci, Sugitani, Toyama 9300194, JapanToyama Med & Pharmaceut Univ, Fac Pharmaceut Sci, Sugitani, Toyama 9300194, Japan
Yakura, T
Muramatsu, W
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机构:Toyama Med & Pharmaceut Univ, Fac Pharmaceut Sci, Sugitani, Toyama 9300194, Japan
Muramatsu, W
Uenishi, J
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机构:Toyama Med & Pharmaceut Univ, Fac Pharmaceut Sci, Sugitani, Toyama 9300194, Japan