Asymmetric synthesis of evoninic acid
Asymmetric synthesis of evoninic acid
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DOI：
10.1016/j.tetlet.2022.153747
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发表时间：
2022-05-10
影响因子：
1.8
通讯作者：
Inoue, Masayuki
中科院分区：
文献类型：
--
作者：
Nagai, Toshiya;Wang, Yinghua;Inoue, Masayuki
依文酸(3)是生物活性二氢-b-沉香呋喃倍半萜的14元双内酯的一个组分。3的独特结构为C2‘，C3’-二取代吡啶和邻近的C7‘S，C8’S-二甲基团。本文报道了一条合成对映体3的新路线。手性恶唑烷酮控制了烯烃氢化的立体化学产物，确定了C7‘S甲基的绝对构型。然后，C7‘S立体中心影响了C8’S-甲基的非对映选择性。
Evoninic acid (3) is a component of a 14-membered bislactone of bioactive dihydro-b-agarofuran sesquiterpenoids. The unique structure of 3 is characterized by C2',C3'-disubstituted pyridine and vicinal C7'S,C8'S-dimethyl groups. Here we report a new synthetic route to enantiopure 3. A chiral oxazolidinone controlled the stereochemical outcome of olefin hydrogenation, establishing the absolute configuration of the C7'S-methyl group. The C7'S-stereocenter then influenced the diastereoselectivity to install the C8'S-methyl group.