Total Synthesis of Gelsedilam by Means of a Thiol-Mediated Diastereoselective Conjugate Addition-Aldol Reaction
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- 作者：Dr. You-Ming Huang ; Dr. Yang Liu ; Dr. Chang-Wu Zheng ; Qiao-Wen Jin ; Lu Pan ; Ren-Ming Pan ; Jun Liu and Prof. Dr. Gang Zhao
- 刊名：Chemistry - A European Journal
- 出版年：2016
- 出版时间：December 19, 2016
- 年：2016
- 卷：22
- 期：51
- 页码：18339-18342
- 全文大小：834K
- ISSN：1521-3765
文摘
The total synthesis of gelsedilam, which features a highly diastereoselective thiol conjugate addition–intramolecular aldol reaction to install the strained and caged [3.2.2] bridged ring system and highly efficient NiCl2/NaBH4-mediated four-step transformation in one-pot to construct its five-membered lactam ring is reported. The synthesis requires only 18 linear steps from the known compounds, providing useful strategies for the construction of the intricate ring system in the synthesis of related gelsedine-type alkaloids.