204 0

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)
Files in This Item:
There are no files associated with this item.
Export
RIS (EndNote)
XLS (Excel)
XML


qrcode

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

BROWSE