Divergent Asymmetric Total Syntheses of (-)-Alloaristoteline and (+)-Aristoteline via Directed Indolization Strategies
- Title
- Divergent Asymmetric Total Syntheses of (-)-Alloaristoteline and (+)-Aristoteline via Directed Indolization Strategies
- Other Titles
- 위치 선택적 인돌화 반응을 통한 (-)-Alloaristoteline과 (+)-Aristoteline의 전합성
- Author
- 전태홍
- Alternative Author(s)
- Tae-Hong Jeon
- Advisor(s)
- 조천규
- Issue Date
- 2023. 8
- Publisher
- 한양대학교
- Degree
- Doctor
- Abstract
- We have previously demonstrated that ene-hydrazides prepared from enol triflates in regiochemically defined form may undergo Fischer indolization reactions without regiochemical scrambling.
As a part of our ongoing research on the regiocontrolled indolization strategy toward indole alkaloid synthesis, we present a new synthetic approach to (-)-alloaristoteline and (+)-aristoteline via directed Fischer indolization strategies. The key common intermediate, doubly-bridged enol triflate, was prepared via a set of reactions including enantioselective deprotonation-silylation and intramolecular Mukaiyama Michael addition. It was successfully bifurcated to complete the first completely synthetic routes to the titled natural alkaloids using late-state directed indolization strategies.
- URI
- http://hanyang.dcollection.net/common/orgView/200000683888https://repository.hanyang.ac.kr/handle/20.500.11754/187343
- Appears in Collections:
- GRADUATE SCHOOL[S](대학원) > CHEMISTRY(화학과) > Theses (Ph.D.)
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