1201668-20-3Relevant academic research and scientific papers
Dipyrone approach toward the synthesis of the cytotoxic natural product auripyrone A
Jung, Michael E.,Salehi-Rad, Ramin
scheme or table, p. 4931 - 4933 (2011/01/04)
An approach to the synthesis of the cytotoxic natural product auripyrone A 1 via the cyclization of an alcohol onto a γ-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 γ-pyrone under normal conditions is very difficult.
Total synthesis of auripyrone a using a tandem non-aldol aldol/ paterson aldol process as a key step
Jung, Michael E.,Salehi-Rad, Ramin
supporting information; experimental part, p. 8766 - 8769 (2010/02/27)
To aldol or non-aldol: The titled reaction sequence generates the polypropionate 3 from the epoxy alcohol 1 and the ketone 2 as a single diastereomer. Compound 2 was used for an efficient synthesis of auripyrone A using a highly regioselective hemiketaliz
