1. Gold-Catalyzed Intramolecular Redox Reaction of N-Sulfonyl Alkynyl Hydroxyl Amines 2. Studies Toward the Synthesis of Meloscine
- Title
- 1. Gold-Catalyzed Intramolecular Redox Reaction of N-Sulfonyl Alkynyl Hydroxyl Amines 2. Studies Toward the Synthesis of Meloscine
- Author
- 소은수
- Alternative Author(s)
- Eunsu So
- Advisor(s)
- 신승훈
- Issue Date
- 2011-02
- Publisher
- 한양대학교
- Degree
- Master
- Abstract
- Part I. Gold-Catalyzed Intramolecular Redox of N-Sulfonyl alkynyl hydroxyl amines
Addition of R2N-OH onto alkyne will lead to alpha-amino carbonyl compounds that constitute a fundamental organic building block. We realized this concept in an intramolecular fashion using alkyne tethered N-sulfonyl hydroxylamines. Depending on the alkynyl substituents, the reaction follows two distinct manifolds, namely the formation of 3-pyrrolidinones and nitrones.
Part II. Studies Toward the Synthesis of Meloscine
Meloscine, one of melodinus alkaloids, was first isolated in 1989 from ethyl 2-oxocyclopentaneacetate by Overman and Robertson. This was studied further by Bach’s group that increased enantioselectivity via photochemical cycloaddition using chiral complexing agent.
Recently, our group published stereoselective one-pot synthesis of 1- aminoindans and 5,6-fused azacycles using gold-catalyzed Redox-Pinacol-Mannich-Michael cascade. This one-pot protocol prompted us to pursue a consice route to the core structure of meloscine in more efficient and stereoselective way. Using this atom-efficient, step-, and redox-economical protocol, we investigated a way to synthesis meloscine from acetoacetanilide.
- URI
- https://repository.hanyang.ac.kr/handle/20.500.11754/139827http://hanyang.dcollection.net/common/orgView/200000415706
- 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