Total Synthesis of Nuclear Factor of Activated T-Cells-68 (NFAT-68): Sequential Use of Chiral Allenylsilane and Titanium Alkoxide-Mediated Reductive Coupling Bond Construction
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- 作者：Bin Cai ; Ryan W. Evans ; Jie Wu ; James S. Panek
- 刊名：Organic Letters
- 出版年：2016
- 出版时间：September 2, 2016
- 年：2016
- 卷：18
- 期：17
- 页码：4304-4307
- 全文大小：339K
- 年卷期：0
- ISSN：1523-7052
文摘
Highly enantioenriched chiral allenylsilanes 4 were prepared in high yield through a scalable synthetic sequence, employing a modified copper-catalyzed SN2′ reaction. These reagents were used for the production of enantioenriched homoproparglylic ethers 5, which were subjected to titanium alkoxide-mediated reductive coupling with acetylenic esters to produce (E,E)-dienes 6 bearing α,β,γ,δ-unsaturated esters. Both enantiomers of nuclear factor of activated T-cells-68 (NFAT-68) were synthesized in five steps with the sequential use of the two methods.