Modular Access to Complex Prodiginines: Total Synthesis of (+)-Roseophilin via its 2-Azafulvene Prototropisomer

作者:Frederich James H; Harran Patrick G*
来源:Journal of the American Chemical Society, 2013, 135(10): 3788-3791.
DOI:10.1021/ja400473v

摘要

Ansa-bridged, prodiginines are bioactive pigments produced by bacteria. Certain of these structures are reported to be antagonists of protein protein interactions involved in apoptosis. We describe a new entry to alkaloids of this type, demonstrated with a concise asymmetric synthesis of (+)-roseophilin (3). Our route constructs the pyrrolophane motif via phosphoryl transfer-terminated macroaldolization and passes through a previously unexplored prototropic form of the natural product.

  • 出版日期2013-3-13