Department of Chemistry, University of California , 1102 Natural Sciences II, Irvine, California 92697-2025, United States , and Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095-1569, United States.
Org Lett. 2013 Dec 6;15(23):6014-7. doi: 10.1021/ol402905n. Epub 2013 Nov 12.
A Diels-Alder 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.
采用 Diels-Alder 反应、去对称化的羟醛缩合反应和还原 Heck 环化反应，进行了与 exiguaquinol 相关的四环的短合成，exiguaquinol 是一种潜在的抗生素。这个高级模型系统和天然产物的基态能量解释了实验中获得的不正确的半缩醛构型，并指出了磺酸盐在决定天然产物相对构型中的重要性。
