Asymmetric Total Synthesis of Propindilactone G, Part 2: Enantioselective Construction of the Fully Functionalized BCDE Ring System
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- 作者：Jia-Jun Zhang ; Dr. Lin You ; Dr. Yue-Fan Wang ; Yuan-He Li ; Xin-Ting Liang ; Bo Zhang ; Dr. Shou-Liang Yang ; Qi Su ; Prof. Dr. Jia-Hua Chen and Prof. Dr. Zhen Yang
- 刊名：Chemistry – An Asian Journal
- 出版年：2016
- 出版时间：May 6, 2016
- 年：2016
- 卷：11
- 期：9
- 页码：1414-1424
- 全文大小：1166K
- ISSN：1861-471X
文摘
The enantioselective synthesis of the fully functionalized BCDE tetracyclic ring system of propindilactone G (A) is reported. Several synthetic methods were developed and applied to achieve this goal, including: 1) an asymmetric Diels–Alder reaction in the presence of Hayashi′s catalyst for the synthesis of optically pure key intermediate 3; 2) an intramolecular Pauson–Khand reaction (PKR) for the stereoselective synthesis of the BCDE ring with an all-carbon chiral quaternary center at the C13 position by using the TMS-substituted acetylene as the substrate; and 3) Pd-catalyzed reductive hydrogenolysis for the stereoselective synthesis of the fully functionalized BCDE tetracyclic ring system. The chemistry developed herein provided a greater understanding of the total synthesis propindilactone G (A) and its analogues.