Gladding Jeffery A, Bacci James P, Shaw Scott A, Smith Amos B
Department of Chemistry, Monell Chemical Senses Center and Laboratory of Research on the Structure of Matter, University of Pennsylvania, Philadelphia, PA 19104, United States.
Tetrahedron. 2011 Sep 2;67(35):6697-6706. doi: 10.1016/j.tet.2011.04.094.
Studies directed towards the synthesis of the architecturally complex marine natural product sporolide B are described. Synthetic analysis suggested advanced hydroquinone and benzodiquinane fragments, which upon elaboration were successfully united via an ester linkage. Macrocyclization studies were then carried out, and although a novel macrocyclization product was obtained, subsequent studies revealed that the tertiary hydroxyls at C(6) and C(10) were sterically encumbered to participate in a successful macrocyclization to furnish sporolide B.
本文描述了针对结构复杂的海洋天然产物sporolide B的合成研究。合成分析表明了高级对苯二酚和苯并二喹烷片段，经精心构建后通过酯键成功结合在一起。然后进行了大环化研究，虽然得到了一种新型大环化产物，但后续研究表明，C(6)和C(10)位的叔羟基在空间上受到阻碍，无法成功参与大环化反应以生成sporolide B。
