Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany.
J Org Chem. 2012 Jan 20;77(2):870-7. doi: 10.1021/jo201883k. Epub 2011 Dec 27.
A divergent, practical, and efficient de novo synthesis of fully functionalized L-colitose (3,6-dideoxy-L-galactose), 2-epi-colitose (3,6-dideoxy-L-talose), and L-rhodinose (2,3,6-trideoxy-L-galactose) building blocks has been achieved using inexpensive, commercially available (S)-ethyl lactate as the starting material. The routes center around a diastereoselective Cram-chelated allylation that provides a common homoallylic alcohol intermediate. Oxidation of this common intermediate finally resulted in the synthesis of the three monosaccharide building blocks.
一种独特、实用且高效的从头合成全功能化 L-岩藻糖（3,6-二脱氧-L-半乳糖）、2-差向异构化 L-岩藻糖（3,6-二脱氧-L-塔洛糖）和 L-洛糖（2,3,6-三脱氧-L-半乳糖）砌块的方法已经实现，使用的起始原料是廉价且市售的（S）-乳酸乙酯。这些路线的核心是立体选择性的 Cram-螯合烯丙基化反应，提供了一个共同的高烯丙醇中间体。该共同中间体的氧化最终导致了三种单糖砌块的合成。
