Lecture: «Pot Economy and Time Economy in the Synthesis of Biologically Active Molecules»
Dr. Yujiro Hayashi (Department of Chemistry, Graduate School of Science, Tohoku University)
CiQUS Seminar Room - 12.15 h.
One-pot operations are an effective method for both carrying out several transformations and forming several bonds in a single-pot, while at the same time cutting out several purifications, minimizing chemical waste generation, and saving time. Thus, a one-pot reaction can be not only efficient, but also green and environmentally friendly, and “poteconomy” should be considered in planning a synthesis.
Hayashi Lab has already reported three pot synthesis of (-)-oseltamivir, a neuraminidase inhibitor used in the treatment of human influenza, based on the diphenylprolinol silyl ether mediated Michael reaction of aldehyde and nitroalkene as a key step. The group has accomplished “onepot” synthesis of (-)-oseltamivir without evaporation nor solvent exchange by the modification of the previous three pot synthesis. Recently they have accomplished 60 minutes total synthesis of (-)-oseltamivir for “time-economy“. The lab further applied one-pot synthetic strategy to the total synthesis of prostaglandin E1 methyl ester, and accomplished three “one-pot” synthesis of this biologically important molecule. Recently (S)-baclofen was synthesized via one-pot sequential reaction from the commercially available compounds.
A recent progress in the one-pot synthesis will be described.
