First asymmetric total syntheses of cernuane-type Lycopodium alkaloids, cernuine, and cermizine D |
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Authors: | Nishikawa Yasuhiro Kitajima Mariko Takayama Hiromitsu |
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Institution: | Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan. |
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Abstract: | The first total syntheses of two cernuane-type Lycopodium alkaloids, (-)-cernuine and (+)-cermizine D, were accomplished starting from (+)-citronellal. The syntheses involved organocatalytic alpha-amination to afford oxazolidinone, which is used for diastereoselective allylation, and asymmetric transfer aminoallylation followed by stereoselective construction of an aminal moiety as key steps. |
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