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论文题目: |
Application of the Helquist Annulation in Lycopodium Alkaloid Synthesis: Unified Total Syntheses of (-)-8-Deoxyserratinine, (-)-Fawcettimine, and (+)-Lycoflexine
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论文题目英文: |
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作者: |
Yang, Yu-Rong; Shen, Liang; Huang, Jiu-Zhong; Xu, Tao; Wei, Kun
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论文出处: |
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年: |
2011
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卷: |
76 |
期: |
10 |
页: |
3684-3690 |
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发表期刊: |
JOURNAL OF ORGANIC CHEMISTRY |
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影响因子: |
3.952
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摘要: |
A unified strategy for total synthesis of the Lycopodium alkaloids (-)-8-deoxyserratinine (7), (+)-fawcettimine (1), and (+)-lycoflexine (4) is detailed. The key features include a highly efficient Helquist annulation to assemble the cis-fused 6/5 bicycle, facile construction of the aza nine-membered ring system employing double N-alkylation strategy, providing access to the common tricyclic skeleton, asymmetric Shi epoxidation, delivering the desired beta-epoxide stereospecifically to furnish (-)-8-deoxyserratinine (7), SmI(2) reduction of dihydroxylation derivative 35 to enable formation of (+)-fawcettimine (1), and a rapid biomimetic transformation of (+)-fawcettimine (1) into (+)-lycoflexine (4) via an intramolecular Mannich cyclization. |
英文摘要: |
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