Sánchez-Abella Laura, Fernández Susana, Armesto Nuria, Ferrero Miguel, Gotor Vicente
Departamento de Química Organica e Inorganica and Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, 33006-Oviedo, Asturias, Spain.
J Org Chem. 2006 Jul 7;71(14):5396-9. doi: 10.1021/jo0606249.
We have developed simple methods that provide a rapid entry into the synthesis of a series of quinate and shikimate analogues, including (-)-methyl 4-epi-shikimate and the 4,5-epoxy analogues of the parent acids. Epoxy derivatives of quinic and shikimic acids were converted into methyl scyllo-quinate and (+)-methyl 3-epi-shikimate, respectively, by processes involving a regio- and stereoselective epoxide ring opening. The strategies described take place through short, high-yield reaction sequences.
我们已经开发出了一些简单的方法，能够快速合成一系列奎尼酸和莽草酸类似物，包括（-）-4-表莽草酸甲酯以及母体酸的4,5-环氧类似物。奎尼酸和莽草酸的环氧衍生物分别通过区域和立体选择性环氧开环反应转化为甲基scyllo-奎尼酸酯和（+）-3-表莽草酸甲酯。所描述的合成策略是通过简短且高产率的反应序列实现的。
