A practical, enantioselective synthetic route to a key precursor to the tetracycline antibiotics
A practical, enantioselective synthetic route to a key precursor to the tetracycline antibiotics
复制标题
DOI：
10.1021/ol071377d
复制
发表时间：
2007-08-30
期刊：
影响因子：
5.2
通讯作者：
Myers, Andrew G.
中科院分区：
文献类型：
--
作者：
Brubaker, Jason D.;Myers, Andrew G.
报道了四环素类抗生素关键前体的一种实用的、对映选择性的合成路线。该路线从商业物质3-羟基-5-异恶唑羧酸甲酯分9步进行（产率21%）。该路线的关键步骤包括二乙烯基锌与3-苄氧基-5-异恶唑甲醛的对映选择性加成和分子内选择性呋喃Diels-Alder环加成反应。所描述的路线提供了超过40克的色谱纯1，具有93% ee。
A practical, enantioselective synthetic route to a key precursor to the tetracycline antibiotics is reported. The route proceeds in nine steps (21% yield) from the commercial substance methyl 3-hydroxy-5-isoxazolecarboxylate. Key steps in the route involve enantioselective addition of divinylzinc to 3-benzyloxy-5-isoxazolecarboxaldehyde and an endo-selective intramolecular furan Diels-Alder cycloaddition reaction. The route described has provided more than 40 g of chromatographically pure 1 with 93% ee.