Synthesis of Dihydroplakortin, 6-<i>epi</i>-Dihydroplakortin, and Their C10-Desethyl Analogues
作者:Sandra Gemma、Emanuele Gabellieri、Salvatore Sanna Coccone、Francesc Martí、Orazio Taglialatela-Scafati、Ettore Novellino、Giuseppe Campiani、Stefania Butini
DOI:10.1021/jo1001559
日期:2010.4.2
The first synthesis of the marine endoperoxide 9,10-dihydroplakortin, of its C10-desethyl analogue, and of their corresponding C6 epimers is described. Stereogenic centers at C4 and at the lateral chain have been stereoselectively synthesized through Evans’ chiral auxiliary chemistry. Moreover, the reported synthesis features a one-pot three-step hydroperoxysilylation/cyclization reaction for the construction
描述了海洋内过氧化物9,10-二氢广场蛋白,其C10-去乙基类似物及其相应的C6差向异构体的第一合成。通过Evans的手性辅助化学方法,立体选择性地合成了C4和侧链的立体中心。此外,所报道的合成特征为用于内过氧化物环体系的构建的一锅三步加氢过氧化甲硅烷基化/环化反应。通过基于Wittig的策略通过二醇裂解产生的醛的同系物可以进入C3处的含酯侧链。