Department of Chemistry and Biochemistry, National Chung Cheng University, Chia-Yi, 621, Taiwan, ROC.
Org Lett. 2010 Feb 19;12(4):776-9. doi: 10.1021/ol902840x.
The first asymmetric total synthesis of (+)-conicol has been achieved via a key step reaction involving the organocatalytic domino oxa-Michael-Michael-Michael-aldol condensation of 2-((E)-2-nitrovinyl)benzene-1,4-diol and alpha,beta-unsaturated aldehydes. Structures of the three-component domino reaction adducts, 20 and 21, including their absolute configurations, were confirmed unambiguously by X-ray analysis. Through this work, the absolute configuration of (+)-conicol was thereby elucidated.
（+）-康扣醇的首次不对称全合成是通过关键步骤反应实现的，该反应涉及 2-（（E）-2-硝基亚乙烯基）-1,4-苯二酚和α，β-不饱和醛的有机催化串联氧化迈克尔加成-迈克尔加成-迈克尔加成-缩合反应。通过 X 射线分析，明确确定了三组分串联反应加合物 20 和 21 的结构及其绝对构型。通过这项工作，阐明了（+）-康扣醇的绝对构型。
