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  • 08월 28일 16시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

Novel synthesis of tetrasubstituted pyrrole by regioselective 1,3-dipolar cycloaddition and spontaneous decarboxylation

등록일
2008년 8월 12일 15시 49분 39초
접수번호
1495
발표코드
34P336포 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
금 <발표Ⅲ>
발표형식
포스터
발표분야
유기화학
저자 및
공동저자
김종훈, 김용주1, 박승범1
서울대학교 화학과, Korea
1서울대학교 화학부, Korea

Many of bioactive natural products or synthetic drugs contain pyrrole moiety as a key skeleton. Pyrrole is one of the well known classes of heterocycle that display remarkable biological activities such as antibacterial, antiviral, anti-inflammatory, antitumor, and antioxidative. Especially lots of tetra- or penta-substituted pyrroles have been identified as anti-inflammatory and anticancer potent drug moiety. As representative example, atorvastatin (Lipitor?) is top-selling drug applied as an antihyperlipidemic agent. Therefore, highly substituted pyrrole has been one of the major targets in synthetic chemistry community. Many synthetic methods have been reported for the novel synthetic protocol exploration of the pyrrole structure, which can be categorized by following; classical Paal–Knorr synthesis, Hantzsch procedure, metal mediated cyclization and various cycloaddition strategies. Whereas these methods have been proven to be useful for the synthesis of pyrrole derivatives, the desired products are associated with regioisomers, especially in the case of cycloaddition strategies, which limits the scope of synthetic modification. However, there are a quite limited number of synthetic reports which can partly control the regioselectivity of pyrrole. Most of the cycloaddition approaches in the literature used symmetric alkynes to bypass the regioselectivity issue or has low regioselectivity with unsymmetrical alkyne or alkene. We designed and synthesized α,β-unsaturated cyclic ketone(1) as a non-symmetric dipolarophile and various Münchnones (1,3-oxazolium-5-olates, 2) as 1,3-dipole for a [3+2] cycloaddition. This system can control the regiochemistry of resulting pyrroles, and the efficiency of this transformation was enhanced by the introduction of microwave-assisted reaction condition. Substituents on pyrrole are derived from aldehydes, amino acids and acylating agents, which means that we can achieve a huge molecular diversity based on pyrrole core skeleton.


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