Regioselective Spirostan E-Ring Opening for the Synthesis of Dihydropyran Steroidal Frameworks
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- 作者：J. Ciciolil Hilario-Martínez ; Reyna Zeferino-Díaz ; Miguel A. Muñoz-Hernández ; Ma. Guadalupe Hernández-Linares ; José Luis Cabellos ; Gabriel Merino ; Jesús Sandoval-Ramírez ; Zhendong Jin ; María A. Fernández-Herrera
- 刊名：Organic Letters
- 出版年：2016
- 出版时间：April 15, 2016
- 年：2016
- 卷：18
- 期：8
- 页码：1772-1775
- 全文大小：280K
- 年卷期：0
- ISSN：1523-7052
文摘
The regioselective opening of the ring E in spirostan sapogenins provides new dihydropyran derivatives. This novel side chain is obtained after a Lewis acid mediated acetolysis followed by an alkaline workup. The reaction mechanism is analyzed via density functional theory computations, and both experimental and computational data support the formation of an oxacarbenium intermediate. The behavior of the title skeletons under acidic conditions is also investigated.