Synthesis of the Tetracyclic Core of Exiguaquinol
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- 作者：Gregg M. Schwarzwalder ; Sarah E. Steinhardt ; Hung V. Pham ; K. N. Houk ; Christopher D. Vanderwal
- 刊名：Organic Letters
- 出版年：2013
- 出版时间：December 6, 2013
- 年：2013
- 卷：15
- 期：23
- 页码：6014-6017
- 全文大小：280K
- 年卷期：v.15,no.23(December 6, 2013)
- ISSN：1523-7052
文摘
A Diels鈥揂lder reaction, a desymmetrizing aldol reaction, and a reductive Heck cyclization are employed in a short synthesis of a tetracycle relevant to exiguaquinol, a potential antibiotic. Ground-state energies of this advanced model system and the natural product rationalize the incorrect hemiaminal configuration experimentally obtained and point to the importance of the sulfonate in dictating the relative configuration of the natural product.