Studies towards total synthesis of (±)tubifolidine via regioselective Fischer indolization
- Title
- Studies towards total synthesis of (±)tubifolidine via regioselective Fischer indolization
- Author
- 김정화
- Alternative Author(s)
- Kim, Jeong Hwa
- Advisor(s)
- 조천규
- Issue Date
- 2019-02
- Publisher
- 한양대학교
- Degree
- Master
- Abstract
- We have previously reported a synthesis of ene-hydrazide from enol triflate and a subsequent indolization reaction as a new entry to the regioselective Fischer indole synthesis.1 In this process, a base-catalyzed intramolecular aza-Michael reaction, in situ trapping of the resulting enolate, and subsequent C-N coupling with phenyl hydrazide afforded the key ene-hydrazides. This new synthetic strategy has been successfully applied to the total synthesis of (+)-aspidospermidine and (-)-tabersonine.2
Toward further development of our strategy, we have envisaged a new synthetic route to (±)-tubifolidine. Buchwald-Hartwig type amination and regioselective Fischer indolization
under Lewis acidic conditions would selectively afford desired indole 2. Presented herein is the progress toward the syntheses of (±)-tubifolidine.; 우리 연구실에서는 enol triflate로 부터 ene-hydrazide를 만들어 indolization 반응
을 통하여 위치 선택성을 가지고 있는 인돌 화합물 합성을 연구해 왔다. 이 방법을
사용하여 (±)-tubifolidine 이라는 천연물 합성을 목표로 하였고 중요 스텝으로는
aza-Michael addition과 triflation을 통하여 만들어진 enol triflate에 Buchwald
Hartwig type amination을 통하여 ene-hydrazide 형태의 화합물 합성을 계획하였고
그 후 Lewis 산 존재 하에 regioselective Fischer indolization을 통하여 원하는 천연
물의 골격을 만들도록 계획하였다. 이후 몇 스텝을 통하여 원하는 천연물인 (±)
tubifolidine를 만드는 것을 목표로 연구를 진행중이다.
- URI
- https://repository.hanyang.ac.kr/handle/20.500.11754/99862http://hanyang.dcollection.net/common/orgView/200000434729
- Appears in Collections:
- GRADUATE SCHOOL[S](대학원) > THEATER & FILM(연극영화학과) > Theses (Master)
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