Cho Chang-Woo, Krische Michael J
University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, Texas 78712, USA.
Org Lett. 2006 Mar 2;8(5):891-4. doi: 10.1021/ol052976s.
Hydrogen-mediated reductive coupling of glyoxal 2 and 1,3-enyne 3 provides alpha-hydroxy ketone 4 in 70% yield and 91% enantiomeric excess. Notably, the benzylic ether and diene side chain of 4 remain intact under the conditions of hydrogen-mediated coupling. In four steps, alpha-hydroxy ketone 4 is converted to pyrans 8 and 9, which embody key structural features of the bryostatin recognition domain.
氢介导的乙二醛2与1,3-烯炔3的还原偶联反应以70%的产率和91%的对映体过量提供了α-羟基酮4。值得注意的是，在氢介导的偶联反应条件下，4的苄基醚和二烯侧链保持完整。经过四步反应，α-羟基酮4转化为吡喃8和9，它们体现了苔藓抑素识别结构域的关键结构特征。
