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제114회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Total synthesis of (±)-lycorine via Diels - Alder reaction of 3,5-dibromo-2-pyrone

등록일
2014년 8월 29일 13시 03분 36초
접수번호
1382
발표코드
ORGN.P-896 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
10월 15일 (수요일) 16:00~19:00
발표형식
포스터
발표분야
유기화학
저자 및
공동저자
신형섭, 박용규, 조천규*
한양대학교 화학과, Korea

Lycorine (1) is a toxic crystalline alkaloid present in various amaryllidaceae plant species that include lycoris, pancratium, narcissus, galanthus, zephyanthes, and haemanthus. Arising from norbelladine in its biosynthesis, lycorine has the pyrrolo[de]phenanthridine framework that is common to many other congeneric natural compounds (Figure 1). It has a wide variety of important biological activities range from the inhibition of growth and cell division in higher plants. Similar to other amaryllidaceae small molecule constituents, such as pancratistatin and trans-dihydronarciclasin, it has attracted much attention for its highly potent antitumor effects, both in vitro and in vivo, as well as in cancer cells that display resistance to proapoptotic stimuli. Such biological importance together with challenging chemistry of lycorine and related alkaloids have induced many synthetic studies and the generation of many structural analogs. As a part of our ongoing study exploring the utility of 3,5-dibromo-2-pyrone in target-oriented synthesis, we have envisioned the pyrrolo[de]phenanthridine skeleton of lycorine and related natural alkaloids could be rapidly constructed from the cycloadduct of 3,5-dibromo-2-pyrone with a styrene type dienophile. Present herein is our path-finding effort that affords the eventual synthesis of (±)-lycorine.


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