Rhodium-Catalyzed <i>Endo</i>-Selective Epoxide-Opening Cascades: Formal Synthesis of (−)-Brevisin
作者:Kurt W. Armbrust、Matthew G. Beaver、Timothy F. Jamison
DOI:10.1021/jacs.5b03570
日期:2015.6.3
an effective catalyst for endo-selective cyclizations and cascades of epoxy-(E)-enoate alcohols, thus enabling the synthesis of oxepanes and oxepane-containing polyethers from di- and trisubstituted epoxides. Syntheses of the ABC and EF ring systems of (-)-brevisin via all endo-diepoxide-opening cascades using this method constitute a formal total synthesis and demonstrate the utility of this methodology
[Rh(CO)2Cl]2 是环氧-(E)-烯醇的内选择性环化和级联反应的有效催化剂,因此能够从二取代和三取代环氧化物合成氧杂环庚烷和含氧杂环己烷的聚醚。(-)-brevisin 的 ABC 和 EF 环系统使用这种方法通过所有内双环氧化物开放级联合成构成正式的全合成,并证明了这种方法在合成海洋阶梯聚醚天然产物的背景下的实用性。