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제118회 대한화학회 학술발표회, 총회 및 기기전시회 안내 A convenient synthesis of tropane ring structure via an oxidative Mannich-type cyclization

2016년 8월 31일 21시 30분 49초
ORGN.P-424 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
10월 14일 (금요일) 11:00~12:30
저자 및
조한별, Ahmed H. E. Hassan1, 이재균2, 조용서3,*, 민선준4,*
한양대학교 응용화학과, Korea
1과학기술연합대학원대학교(UST) 화학과, Egypt
2한국과학기술연구원(KIST) 케모인포매틱스연구단, Korea
3한국과학기술연구원(KIST) 생체과학연구본부, Korea
4한양대학교 과학기술대학/응용화학과, Korea
Tropane alkaloids are a group of alkaloids generally derived from natural plants and they contain a unique azabicyclic[3.2.1]octane ring structure. They are often found as secondary metabolites in many members of the plant families such as Erythroxylaceae and Solanaceae. The alkaloid analogues which include tropane structure have been manufactured as active pharmaceutical ingredients (APIs) for a long time. In particular, several tropane derivatives can regulate biological receptors associated with neurotransmission, which may be useful for the treatment of neurological or psychological disorders. Therefore, the tropane alkaloids are highly attractive targets to organic chemists due to their pharmacological importance as well as structural complexity. In this study, our synthetic approaches towards tropane alkaloids via oxidative Mannich cyclization were described. Our synthetic plan includes oxidative coupling reaction of cyclic amine with acetone followed by intramolecular Mannich-type cyclization to afford tropane core structure. In this event, direct C-H activation of cyclic amine by an oxidant to generate the corresponding iminium intermediate is a crucial transformation for consecutive C-C bond formations, which will be focused on in this presentation. In addition, development of a chemical library of tropane derivatives will be further discussed.