Department of Chemistry, Temple University, 1901 North 13th Street, Philadelphia, Pennsylvania 19122, United States.
Org Lett. 2011 Apr 1;13(7):1787-9. doi: 10.1021/ol2002978. Epub 2011 Mar 7.
A five-step assembly of silicon-protected dipeptide mimics from commercially available reagents is described. This methodology makes silanediol protease inhibitors readily available for the first time. The sequence features asymmetric hydrosilylation, a novel reduction of a silyl ether to a silyllithium reagent, and addition of this dianion to a sulfinimine, to produce the complete inhibitor skeleton with full control of stereochemistry. Oxidation of the primary alcohol to an acid completes the synthesis.
本文描述了一种从商业可得试剂出发，经五步合成硅保护二肽类似物的方法。这种方法使硅烷二醇蛋白酶抑制剂首次得以大量制备。该方法的关键步骤包括不对称硅氢化反应、首例硅醚还原为硅锂试剂、二负离子与亚磺亚胺的加成反应，从而以完全立体控制的方式构建出完整的抑制剂骨架。然后，通过氧化伯醇至羧酸完成全合成。
