Department of Chemistry, University of California, Irvine, California 92697, USA.
J Am Chem Soc. 2010 Mar 3;132(8):2542-3. doi: 10.1021/ja910809c.
The first enantioselective synthesis of a member of the chlorosulfolipid family of natural products is reported. All of the polar substituents of malhamensilipin A are introduced with high stereoselectivity, and the unique (E)-chlorovinyl sulfate is created by a chemo-, regio-, and stereoselective E2 elimination of HCl in a reaction that likely has a counterpart in the biosynthesis of this fascinating natural product.
首次报道了一种氯磺酸脂类天然产物的对映选择性合成。马拉门斯林 A 的所有极性取代基均具有高立体选择性地引入,独特的(E)-氯代乙烯基硫酸盐是通过反应中 HCl 的化学选择性、区域选择性和立体选择性 E2 消除形成的,该反应可能在这种迷人的天然产物的生物合成中具有对应物。