ter Horst Bjorn, Feringa Ben L, Minnaard Adriaan J
Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborg 4, 9747AG, Groningen, The Netherlands.
Org Lett. 2007 Aug 2;9(16):3013-5. doi: 10.1021/ol071078o. Epub 2007 Jul 14.
The first total synthesis of phthioceranic acid (1) has been achieved by an iterative catalytic asymmetric 1,4-addition protocol. This method provides a robust and high-yielding route for the preparation of 1,3-oligomethyl (deoxypropionate) arrays. After the desired number of methyl groups has been introduced, these arrays can be further functionalized at both ends to polymethyl-substituted lipids such as phthioceranic acid, a heptamethyl-branched fatty acid from the virulence factor Sulfolipid-I (2), found in Mycobacterium tuberculosis.
通过迭代催化不对称1,4-加成方案首次实现了结核硬脂酸（1）的全合成。该方法为制备1,3-低聚甲基（脱氧丙酸酯）阵列提供了一条稳健且高产率的路线。在引入所需数量的甲基后，这些阵列两端可进一步官能化，得到多甲基取代的脂质，如结核硬脂酸，一种来自结核分枝杆菌毒力因子硫脂-I（2）的七甲基支链脂肪酸。
