Studies toward Asymmetric Total Synthesis of Subincanadine F via semi-Pinacol Rearrangement
- Title
- Studies toward Asymmetric Total Synthesis of Subincanadine F via semi-Pinacol Rearrangement
- Author
- 민혜원
- Advisor(s)
- 조천규
- Issue Date
- 2023. 2
- Publisher
- 한양대학교
- Degree
- Master
- Abstract
- Subincanadine F is a novel indole alkaloid possessing a bridged medium-sized heterocyclic framework, isolated in 0.002% yield as a trifluoroacetic acid salt from a Brazilian medicinal plant, Aspidosperma subincanum. The 1-azabicyclo[4,3,1]decane skeleton embedded in this alkaloid imposes a formidable synthetic challenge. Recently, we found that perhydrocyclohepta[b]indole-6,7-diol can undergo a semi-pinacol-type rearrangement into ring-contracted 1-formyl perhydro-carbazole. Moreover, the asymmetric introduction of the 6,7-diol group effectively controlled the stereochemistry of the formyl group. The scope and limitation of this potentially useful alternative to Koser’s reagent-based method were investigated, along with the application to the asymmetric total synthesis of subincanadine F.
- URI
- http://hanyang.dcollection.net/common/orgView/200000652000https://repository.hanyang.ac.kr/handle/20.500.11754/179490
- Appears in Collections:
- GRADUATE SCHOOL[S](대학원) > CHEMISTRY(화학과) > Theses (Master)
- Files in This Item:
There are no files associated with this item.
- Export
- RIS (EndNote)
- XLS (Excel)
- XML