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.