Shing Tony K M, Cheng Hau M
Department of Chemistry and Center of Novel Functional Molecules, The Chinese University of Hong Kong, Shatin, Hong Kong, China.
J Org Chem. 2007 Aug 17;72(17):6610-3. doi: 10.1021/jo0709697. Epub 2007 Jul 19.
A short synthesis of gabosine I (1) from delta-D-gluconolactone (3) in four steps, involving a one-pot TPAP oxidation-K2CO3-mediated intramolecular Horner-Wadsworth-Emmons (HWE) olefination as the key step, is described. Regioselective acetylation of the primary alcohol in gabosine I (1) then furnished gabosine G (2).
描述了以δ-D-葡萄糖酸内酯（3）为原料，经四步反应短合成加波辛I（1）的方法，其中关键步骤是一锅法的四丙基氢氧化铵五水合物（TPAP）氧化-K2CO3介导的分子内霍纳-沃兹沃思-埃蒙斯（HWE）烯化反应。加波辛I（1）中伯醇的区域选择性乙酰化反应随后得到了加波辛G（2）。
