121st General Meeting of the KCS

Type Poster Presentation
Area Organic Chemistry
Room No. Event Hall
Time 4월 19일 (목요일) 11:00~12:30
Code ORGN.P-454
Subject Efficient synthesis of methopholine and Homoprotoberberine Analog through double addition of alkyl halides on DHIQ
Authors Yuri CHoi, PILHO KIM1,*, jae du ha2, Sung Yun Cho2, Jong Yeon Hwang1, Raghavendra Achary1, Gangadhar Rao Mathi1, Dagyum Yoo3
Medicinal Chemistry and Pharmacology, University of Science & Technology, Korea
1Center for Medicinal Chemistry, Korea Research Institute of Chemical Technology, Korea
2WCI, Korea Research Institute of Chemical Technology, Korea
3Korea Research Institute of Chemical Technology, Korea
Abstract Natural and pharmaceutical products containing tetrahydroisoquinolines (THIQs) possess a wide range of biological activities. For the synthesis of diverse THIQs, one of the major precursors utilized is dihydroisoquinolines (DHIQs). Recently, we developed a one-pot double addition chemistry introducing alkyl halides at the C1-methyl and amine positions of DHIQs through double addition of alkyl halides on C1-methyl substituted DHIQs. This chemistry was compatible with various alkyl halides and DHIQs. In a similar context, this chemistry was applied in an intramolecular way for the synthesis of homoprotoberberine. Various analogs of homoprotoberberine can be synthesized using this methodology. The scope and limitation of this chemistry will be discussed.
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