A Convergent Approach toward the C1-C11 Subunit of Phoslactomycins and Formal Synthesis of Phoslactomycin B
A Convergent Approach toward the C1-C11 Subunit of Phoslactomycins and Formal Synthesis of Phoslactomycin B
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DOI：
10.1021/ol8029142
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发表时间：
2009-02-19
期刊：
影响因子：
5.2
通讯作者：
Cossy, Janine
中科院分区：
文献类型：
--
作者：
Druais, Valerie;Hall, Michael J.;Cossy, Janine
光生菌素C1-C11亚基的制备，以及光生菌素B的正式合成，是通过在α -烷氧酮上加入炔基格氏试剂进行螯合控制的聚合策略实现的。乙炔酮的催化对映选择性还原和[2,3]-Wittig重排是控制C4、C5和C9立体中心构型的关键步骤。
The preparation of the C1-C11 subunit of phoslactomycins, and a formal synthesis of phoslactomycin B, were achieved by a convergent strategy involving the chelation-controlled addition of an alkynyl Grignard reagent to an alpha-alkoxy ketone. Catalytic enantioselective reductions of acetylenic ketones and a [2,3]-Wittig rearrangement were utilized as key steps to control the configuration of the C4, C5, and C9 stereocenters.