Buffet Marianne F, Dixon Darren J, Ley Steven V, Reynolds Dominic J, Storer R Ian
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK CB2 1EW.
Org Biomol Chem. 2004 Apr 21;2(8):1145-54. doi: 10.1039/b316858a. Epub 2004 Mar 18.
Tetrahydropyran and tetrahydrofuran containing natural products, drugs and agrochemicals often possess carbon-carbon bonds adjacent to the heteroatom. Consequently, new methods for the construction of anomeric carbon-carbon bonds are of considerable importance. We have devised a new strategy to access these systems that requires the treatment of O-glycoside alkynyl tributylstannane derivatives of furanyl and pyranyl lactols with Lewis acid to effect oxygen to carbon rearrangements. This leads to the formation of the corresponding carbon linked alkynol products that can be further manipulated to produce key structural motifs and building blocks for the assembly of complex molecules.
含有四氢吡喃和四氢呋喃的天然产物、药物及农用化学品通常在杂原子相邻位置含有碳-碳键。因此，构建异头碳-碳键的新方法具有相当重要的意义。我们设计了一种新策略来合成这些体系，该策略需要用路易斯酸处理呋喃基和吡喃基乳糖醇的O-糖苷炔基三丁基锡衍生物，以实现氧到碳的重排。这会导致形成相应的碳连接炔醇产物，这些产物可进一步进行操作，以生成用于组装复杂分子的关键结构基元和构件。
