Application and Scope of Schreiber's Gold(I)-Catalyzed alpha-Pyrone Synthesis to Ring A Aromatic Podolactones

作者：Sanchez Larios Eduardo; Giacometti Robert D; Hanessian Stephen^*

来源：European Journal of Organic Chemistry, 2014, 2014(26): 5664-5669.

DOI：10.1002/ejoc.201402803

• Pyrones
• Anticancer agents
• Terpenoids
• Lactones
• Homogeneous catalysis
• Gold

Schreiber's gold(I)-catalyzed synthesis of alpha-pyrones was adapted to the total synthesis of a ring A aromatic podolactone, urbalactone. The scope of the acetylenic ester partner in the formation of alpha-pyrones was studied. The total synthesis features, as key steps, alpha-pyrone formation, Friedel-Crafts cyclization, Stille coupling, and a N,N'-dicyclohexylcarbodiimide/4-(N, N-dimethylamino) pyridine lactonization to generate the gamma-lactone. Several alpha-pyrone intermediates from this work exhibited in vitro antiproliferative activity against the A2780 ovarian cancer cell line.

• 出版日期2014-9