James Clint A, Coelho Antonio Luiz, Gevaert Matt, Forgione Pat, Snieckus Victor
Department of Chemistry, University of Waterloo, Waterloo, ON, Canada N2L 3G1.
J Org Chem. 2009 Jun 5;74(11):4094-103. doi: 10.1021/jo900146d.
A concise synthesis of heteroaryl dibenzopyranones 9a,b, 10a,b, 11a-c, and 12a-c has been achieved by the LDA-induced migration of heterobiaryl O-carbamates 18, 21, 25, and 30 which, in turn, were prepared in good yield using a combined directed ortho lithiation (DoM)-transition-metal-catalyzed Suzuki cross-coupling strategy. An efficient and general route to a wide variety of heterocycles including coumestans 19a,c and the previously unknown isothiocoumestan ring system 22b has been thereby achieved.
通过LDA诱导的杂二芳基O-氨基甲酸酯18、21、25和30的迁移，实现了杂芳基二苯并吡喃酮9a、b，10a、b，11a - c和12a - c的简洁合成，而这些杂二芳基O-氨基甲酸酯又采用定向邻位锂化（DoM）-过渡金属催化的铃木交叉偶联策略以良好的产率制备得到。由此实现了一条高效且通用的路线，可用于合成包括香豆雌酚19a、c以及此前未知的异硫代香豆雌酚环系22b在内的多种杂环化合物。
