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  • 09월 01일 18시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

제118회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Intramolecular Fischer indole synthesis for the direct synthesis of 3,4-fused tricyclic indole and application to the total synthesis of (-)-aurantioclavine

2016년 9월 2일 11시 40분 16초
ORGN.P-443 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
10월 14일 (금요일) 11:00~12:30
저자 및
박준, 김동현, DAS TAPAS, 조천규*
한양대학교 화학과, Korea
We have previously demonstrated that aryl hydrazides are effective surrogates of aryl hydrazines, undergoing various reactions including the Fischer indole synthesis to afford the corresponding indoles, when treated with enolizable aldehydes and ketones in the presence of an acid. Unlike aryl hydrazines, the aryl hydrazides are readily accessed from aryl halides via the Pd(0) or Cu(I)-catalyzed coupling reaction with N-Boc hydrazine. We have also reported that N-Cbz-aryl hydrazide can proceed in a Fischer indolization reaction to give N-Cbz-indole without the elimination of N-Cbz group. Prompted by our recent interest on 3,4-fused tricyclic indole alkaloids, we set out to study the intramolecular Fischer indolization reaction. Recently, we found that the aryl hydrazides with a ketone or aldehyde containing side chains linked to the meta-position of the aromatic ring undergo acid promoted intramolecular Fischer indole synthesis (IMFIS) to generate 3,4-fused tricyclic indoles. The preparative utility of this conceptually new synthetic approach, which does not require cumbersome prefunctionalization of the indole ring, was demonstrated by its application to a concise synthesis of (-)-aurantioclavine. Further applications of this method to structurally more complex polycyclic indole natural products with 3,4-fused tricyclic indole core are now under study.