Department of Chemistry, University of Ioannina, Section of Organic Chemistry and Biochemistry, 451 10 Ioannina, Greece.
Org Lett. 2012 Jan 20;14(2):584-7. doi: 10.1021/ol203196n. Epub 2012 Jan 10.
A new mild method has been devised for generating o-(naphtho)quinone methides via fluoride-induced desilylation of silyl derivatives of o-hydroxybenzyl(or 1-naphthylmethyl) nitrate. The reactive o-(naphtho)quinone methide intermediates were trapped by C, O, N, and S nucleophiles and underwent "inverse electron-demand" hetero-Diels-Alder reaction with dienophiles to give stable adducts. The method has useful potential application in natural product synthesis and drug research.
一种新的温和方法已经被设计出来，用于通过氟化物诱导的 o-羟基苄基（或 1-萘甲基）硝酸盐的硅基衍生物的去硅化来生成 o-（萘并）醌甲叉。反应性的 o-（萘并）醌甲叉中间体被 C、O、N 和 S 亲核试剂捕获，并与亲二烯体发生“反向电子需求”杂 Diels-Alder 反应，生成稳定的加合物。该方法在天然产物合成和药物研究中有有用的潜在应用。
