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제118회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Asymmetric total syntheses of (+)-aspidospermidine and (-)-tabersonine via regio-controlled Fischer indole synthesis

등록일
2016년 9월 2일 11시 47분 44초
접수번호
2504
발표코드
ORGN.P-445 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
10월 14일 (금요일) 11:00~12:30
발표형식
포스터
발표분야
유기화학
저자 및
공동저자
조현규, 김주영, 조천규*
한양대학교 화학과, Korea
Recently we have demonstrated that ene-hydrazide readily available from enol triflate in regiochemically defined form may undergo Fischer indolization reaction with no regiochemical scrambling. In order to prove its usefulness, we then started to apply our new method to the syntheses of various aspidosperma alkaloids. The aspidosperma family comprises the largest group of indole alkaloids, with more than 250 compounds. The structural challenge posed by these alkaloids in conjunction with the potent pharmacological properties exhibited by several members has stimulated considerable effort directed toward their synthesis. Prior to syntheses of a variety of intricate aspidosperma alkaloids, we initiated synthesis of (+)-aspidospermidine, the simplest aspidosperma alkaloid. With carbamate 1 in hand, the carbamic anion mediated Michael addition followed by triflation gave us bicyclic compound 2 in high yield. Subsequent regioselective Fischer indolization under Lewis acidic conditions culminated in the synthesis of (+)-aspidospermidine 3. It substantiated that our strategy is indeed quite efficient in the syntheses of aspidosperma alkaloids. Based on the initial success, we are investigating the syntheses of other more complicated aspidosperma alkaloids. Presented herein are the total synthesis of (+)-aspidospermidine and our recent progress toward (-)-tabersonine.

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