- Concise asymmetric total synthesis of lycopodine and flabelliformine via cascade cyclization reaction
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The shortest asymmetric total synthesis of lycopodine (3) and the first asymmetric total synthesis of flabelliformine (4) were accomplished by a strategy that features a cascade cyclization of linear substrate (5) to construct tetracyclic structure (6).
- Wada, Kentaro,Kogure, Noriyuki,Kitajima, Mariko,Takayama, Hiromitsu
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p. 187 - 190
(2018/12/11)
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- Protecting-Group-Free Total Synthesis of (-)-Lycopodine via Phosphoric Acid Promoted Alkyne Aza-Prins Cyclization
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A protecting-group-free route for the total synthesis of (-)-lycopodine was demonstrated in only 8 steps from Wade's fawcettimine enone (12 steps from commercial availiable (R)-(+)-pulegone). The key core of this alkaloid was constructed through a phosphoric acid promoted and highly stereocontrolled alkyne aza-Prins cyclization reaction, synchronously establishing the bridged B-ring and the C13 quaternary stereocenter. Importantly, the synthesis further features a new efficient approach for the preparation of other lycopodine-type alkaloids.
- Ma, Donghui,Zhong, Zhuliang,Liu, Zaimin,Zhang, Mingjie,Xu, Shiyan,Xu, Dengyu,Song, Dengpeng,Xie, Xingang,She, Xuegong
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p. 4328 - 4331
(2016/11/09)
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- Development of an enantioselective route toward the lycopodium alkaloids: Total synthesis of lycopodine
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(Figure presented) Synthesis of a C15-desmethyl tricycle core of lycopodine has been accomplished. Key steps in the synthetic sequence include organocatalytic, intramolecular Michael addition of a keto sulfone and a tandem 1,3-sulfonyl shift/Mannich cyclization to construct the tricyclic core ring system. Synthetic work toward this natural product family led to the development of N-(p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide, an organocatalyst which facilitiates enantioselective, intramolecular Michael additions. A detailed mechanistic discussion is provided for both the intramolecular Michael addition and the sulfone rearrangement. Finally, the application of these discoveries to the enantioselective total synthesis of alkaloid lycopodine is described.
- Yang, Hua,Carter, Rich G.
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supporting information; experimental part
p. 4929 - 4938
(2010/10/21)
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- Enantioselective total synthesis of lycopodine
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The first enantioselective total synthesis of lycopodine has been completed. Key steps include a highly diastereoselective organocatalyzed cyclization of a keto sulfone to establish the key C7 and C8 stereocenters and a tandem 1,3-su
- Yang, Hua,Carter, Rich G.,Zakharov, Lev N.
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supporting information; experimental part
p. 9238 - 9239
(2009/02/03)
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- THE TOTAL SYNTHESIS OF LYCOPODINE USING BRIDGEHEAD INTERMEDIATES
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The total synthesis of lycopodine has been achieved by two different routes.In one route a bridgehead carbocation is trapped by 3-benzyloxy-1-propanamine.In the second route a bridgehead enone is generated in situ and reacted with 3-hydroxy-1-propanamine.
- Kraus, George A.,Hon, Yung-Son
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p. 377 - 386
(2007/10/02)
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- A Further Synthesis of (+/-)-Lycopodin
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The synthesis of (+/-)-lycopodin from 2-cyanoethyl-5-methyl-1,3-cyclohexanedione (2b) in six steps is described.An important step is the stereoselective 1,3-annulation reaction of the unsaturated imine 4b with acetone dicarboxylic acid yielding the tricyc
- Schumann, Dieter,Mueller, Hans-Juergen,Naumann, Anneliese
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p. 1700 - 1705
(2007/10/02)
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