一种对映选择性酶促去对称化途径合成六氢-4-呋喃并吡喃醇，它是HIV-1蛋白酶抑制剂的高亲和力配体。
An enantioselective enzymatic desymmetrization route to hexahydro-4-furopyranol, a high-affinity ligand for HIV-1 protease inhibitors.
作者信息
Ghosh Arun K, Sarkar Anindya
机构信息
Department of Chemistry and Department of Medicinal Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 479 07, United States.
出版信息
Tetrahedron Lett. 2017 Aug 16;58(33):3230-3233. doi: 10.1016/j.tetlet.2017.07.010. Epub 2017 Jul 3.
Abstract
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.
摘要
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。
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