Asymmetric total synthesis of a pentacyclic lycopodium alkaloid: huperzine-q |
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| Authors: | Nakayama Atsushi Kogure Noriyuki 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) http://www.p.chiba-u.ac.jp/lab/seitai/index.html. |
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| Abstract: | Right on Q: The first asymmetric total synthesis of (-)-huperzine-Q, which possesses six stereogenic centers and a spiroaminal moiety, has been achieved in 19 steps and 16.4?% overall yield. This synthesis involved a novel stereoselective Pauson-Khand reaction, a vinyl Claisen rearrangement, and a biomimetic spiroaminal formation. TBDPS=tert-butyldiphenylsilyl. |
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| Keywords: | alkaloids natural products Pauson–Khand reaction rearrangement total synthesis |
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