Grainger Richard S, Owoare Richard B
Department of Chemistry, King's College London, Strand, London WC2R 2LS.
Org Lett. 2004 Aug 19;6(17):2961-4. doi: 10.1021/ol048911r.
Two methods to achieve the formal aldol reaction between acetone and two oxabicyclic [3.2.1] ketones are reported. The trimethylsilyl-protected beta-hydroxy ketones are converted by a Wittig reaction into vinyl chlorides as synthetic precursors to alkylidenecarbenes. Selective 1,5 C-H over 1,5 O-Si insertion has been applied to the synthesis of a model for the ABC ring system of ingenol.
报道了两种实现丙酮与两种氧杂双环[3.2.1]酮之间的形式醛醇缩合反应的方法。三甲基硅基保护的β-羟基酮通过维蒂希反应转化为氯乙烯，作为亚烷基卡宾的合成前体。已将选择性的1,5 C-H插入而非1,5 O-Si插入应用于合成 ingenol 的 ABC 环系统模型。
