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Studies toward total synthesis of apparicine

Title
Studies toward total synthesis of apparicine
Author
박재용
Alternative Author(s)
박재용
Advisor(s)
조천규
Issue Date
2022. 2
Publisher
한양대학교
Degree
Master
Abstract
In our recent report, we have demonstrated that azacyclooctenyl triflate affords the corresponding ene-hydrazine via C-N cross coupling using Cu(I) catalyst, and the subsequent Lewis-acid mediated-indolization reaction leads to the formation of the indole product. This new synthetic strategy has been successfully applied to the formal synthesis of (-)-lundurine A. For further development of our strategy, we devised a new synthetic route to a monoterpenoid indole alkaloid apparicine containing an 8-membered ring. The key elaborations are the generation of the azabicyclic compound from the Rh-catalyzed 1,4-addition of pinacolboronate to the 8-memebered cyclic enone, and subsequent intramolecular amide coupling. Copper-catalyzed C-N coupling of enol triflate and indolization using Lewis acid would allow us to complete the total synthesis of apparicine. Herein, the progress toward the synthesis of apparcine and future plans for the completion of the synthesis were summarized. |우리 연구실에서는 구리 촉매를 이용하여 7,8각 고리 enol triflate로부터 ene-hydrazide를 만들고, 그에 상응하는 인돌 화합물의 위치선택적인 합성을 연구해왔다. 이 방법을 사용하여 apparicine 이라는 천연물의 전합성을 목표로 하였으며 중요 스텝으로는 Rh catalized 1,4-addition을 통해 고리 화합물에 가지를 도입할 수 있었으며 그 후 루이스산 존재 하에 위치선택적인 피셔인돌화를 통해 원하는 천연물의 골격을 합성할 수 있었다. 이후, apparicine을 합성하기 위한 주요 반응은 intramolecular amide coupling, reduction, allylic oxidation 반응 등이 있다. 우리는 여기에 현재까지 얻은 결과와 앞으로의 방향에 대해 제시한다.
URI
http://hanyang.dcollection.net/common/orgView/200000590933https://repository.hanyang.ac.kr/handle/20.500.11754/167579
Appears in Collections:
GRADUATE SCHOOL[S](대학원) > CHEMISTRY(화학과) > Theses (Master)
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