Total synthesis of (-)-8-deoxyserratinine via an efficient Helquist annulation and double N-alkylation reaction.
Total synthesis of (-)-8-deoxyserratinine via an efficient Helquist annulation and double N-alkylation reaction.
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DOI：
10.1021/ol1012444
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发表时间：
2010-06
期刊：
影响因子：
5.2
通讯作者：
Yu-Rong Yang;Zengwei Lai;Liang Shen;Jiu-Zhong Huang;Xingxing Wu;Jun-Lin Yin;Kun Wei
中科院分区：
文献类型：
--
作者：
Yu-Rong Yang;Zengwei Lai;Liang Shen;Jiu-Zhong Huang;Xingxing Wu;Jun-Lin Yin;Kun Wei
以烯酮4为原料，经15步反应，首次实现了(-)-8-脱氧丝氨酸的对映选择性全合成，总收率7%。其主要特点包括高效的Helquist环状结构以提供顺式熔融6/5自行车，采用双N-烷基化策略的氮杂九元环体系的简易构建，以及不对称SHI环氧化，以立体专一的方式提供所需的β-环氧化物。
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 beta-epoxide stereospecifically.