Dipyrone approach toward the synthesis of the cytotoxic natural product auripyrone A

作者：Jung Michael E^*; Salehi Rad Ramin

来源：Tetrahedron Letters, 2010, 51(38): 4931-4933.

DOI：10.1016/j.tetlet.2010.07.034

An approach to the synthesis of the cytotoxic natural product auripyrone A 1 via the cyclization of an alcohol onto a gamma-pyrone in 3 is described. The bis(pyrone) alcohol 3 was prepared efficiently from the advanced aldolate 4 via silyl ether cleavage, oxidation, pyrone formation, and PMB ether removal. Instead of providing auripyrone A 1, the attempted cyclization of 3 gave the product of 1,5-acyl migration 8. Model studies show this to be a general process: therefore, cyclization of an alcohol on such a hindered gamma-pyrone under normal conditions is very difficult.

• 出版日期2010-9-22