Ghosh Arun K, Sarkar Anindya
Department of Chemistry and Department of Medicinal Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 479 07, United States.
Tetrahedron Lett. 2017 Aug 16;58(33):3230-3233. doi: 10.1016/j.tetlet.2017.07.010. Epub 2017 Jul 3.
An enantioselective synthesis of (a,,a)-hexahydro-4-furo[2,3-]pyran-4-ol, a high-affinity nonpeptide ligand for a variety of potent HIV-1 protease inhibitors is described. The key steps involved a highly enantioselective enzymatic desymmetrization of -diacetate, an efficient transacetalization, and a highly diastereoselective reduction of a ketone. This route is amenable to large-scale synthesis using readily available starting materials.
描述了一种对映选择性合成（α，α）-六氢-4-呋喃并[2,3-c]吡喃-4-醇的方法，它是多种强效HIV-1蛋白酶抑制剂的高亲和力非肽配体。关键步骤包括对二乙酸酯进行高度对映选择性的酶促去对称化、高效的转缩醛化反应以及对酮进行高度非对映选择性的还原。该路线适用于使用易得起始原料的大规模合成。
