Total Synthesis of (−)-8-Deoxyserratinine via an Efficient Helquist Annulation and Double N-Alkylation Reaction

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• 作者：Yu-Rong Yang ; Zeng-Wei Lai ; Liang Shen ; Jiu-Zhong Huang ; Xing-De Wu ; Jun-Lin Yin ; Kun Wei
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：August 6, 2010
• 年：2010
• 卷：12
• 期：15
• 页码：3430-3433
• 全文大小：207K
• 年卷期：v.12,no.15(August 6, 2010)
• ISSN：1523-7052

文摘

The first enantioselective total synthesis of (−)-8-deoxyserratinine has been achieved in 15 steps from enone 4 with 7% overall yield. The key features include a highly efficient Helquist annulation to furnish the cis-fused 6/5 bicycle, facile construction of the aza nine-membered ring system employing double N-alkylation strategy, as well as asymmetric Shi epoxidation, delivering the desired β-epoxide stereospecifically.