Akindele Tito, Marsden Stephen P, Cumming John G
School of Chemistry, University of Leeds, Leeds LS2 9JT, U.K.
Org Lett. 2005 Aug 18;7(17):3685-8. doi: 10.1021/ol051292h.
The condensation of substituted allylsiloxanes with aldehydes leads to the highly stereoselective construction of 2,3,4,5-tetrasubstituted tetrahydrofurans. With electron-rich aryl and alpha,beta-unsaturated aldehydes as substrates, the stereochemical outcome at C5 can be dictated by appropriate choice of Lewis acid. The reaction has been applied to a concise (nine step) synthesis of (+)-virgatusin (ent-1). [reaction: see text]
取代烯丙基硅氧烷与醛的缩合反应能高度立体选择性地构建2,3,4,5-四取代四氢呋喃。以富电子芳基和α,β-不饱和醛为底物时，通过适当选择路易斯酸可以决定C5位的立体化学结果。该反应已应用于(+)-virgatusin（对映体-1）的简洁（九步）合成中。[反应：见正文]
