Evolution of a synthetic strategy:: Total synthesis of (±)-Welwitindolinone A isonitrile
Evolution of a synthetic strategy:: Total synthesis of (±)-Welwitindolinone A isonitrile
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DOI：
10.1021/ja076663z
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发表时间：
2008-02-13
影响因子：
15
通讯作者：
Wood, John L.
中科院分区：
文献类型：
--
作者：
Reisman, Sarah E.;Ready, Joseph M.;Wood, John L.
描述了天然产物(+/-)-威氏吲哚酮A异腈(1)的高效、高立体选择性全合成。通过区域选择性和非对映选择性的[2+2]烯酮环加成建立了1的双环[4.2.0]辛烷核。通过氯离子介导的半匹纳柯重排，在一次操作中安装了C12季中心和邻立体原氯，具有良好的立体控制效果。所描述的构建螺-吲哚的策略包括SMl(2)-LiCl介导的还原环化和同时构建螺-吲哚和乙烯基异腈部分的新型阴离子环化。
An efficient and highly stereoselective total synthesis of the natural product (+/-)-welwitindolinone A isonitrile (1) is described. The bicyclo[4.2.0]octane core of 1 was established by a regio- and diastereoselective [2+2] ketene cycloaddition. The C12 quaternary center and vicinal stereogenic chlorine were installed in a single operation with excellent stereocontrol via a chloronium ion mediated semipinacol rearrangement. Described strategies for construction of the spiro-oxinole include a SMl(2)-LiCl mediated reductive cyclization and a novel anionic cyclization that simultaneously constructs the spiro-oxindole and vinyl isonitrile moieties.