Asymmetric Synthesis of (-)-6-Desmethyl-Fluvirucinine A(1) via Conformationally-Controlled Diastereoselective Lactam-Ring Expansions
- Authors
- Moon, Hyunyoung; Yoon, Hojong; Lim, Changjin; Jang, Jaebong; Yi, Jong-Jae; Lee, Jae Kyun; Lee, Jeeyeon; Na, Younghwa; Son, Woo Sung; Kim, Seok-Ho; Suh, Young-Ger
- Issue Date
- 2018-09
- Publisher
- MDPI
- Citation
- MOLECULES, v.23, no.9
- Abstract
- The versatile synthesis of (-)-6-desmethyl-fluvirucinine A(1) was accomplished at a 24% overall yield through a thirteen-step process from a known vinylpiperidine. The key part involved the elaboration of the distal stereocenters and a macrolactam skeleton via conformationally-induced diastereocontrol and the iterative aza-Claisen rearrangements of lactam precursors.
- Keywords
- INFLUENZA-A VIRUS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; AZA-CLAISEN REARRANGEMENT; N,O-ACETAL TMS ETHER; ANTHELMINTIC MACROLACTAMS; VERSATILE CONVERSION; SCH 38516; FLUVIRUCIN-B2; ALKALOIDS; AGLYCON; INFLUENZA-A VIRUS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; AZA-CLAISEN REARRANGEMENT; N,O-ACETAL TMS ETHER; ANTHELMINTIC MACROLACTAMS; VERSATILE CONVERSION; SCH 38516; FLUVIRUCIN-B2; ALKALOIDS; AGLYCON; fluvirucinine; aza-Claisen rearrangement; amidoalkylation
- ISSN
- 1420-3049
- URI
- https://pubs.kist.re.kr/handle/201004/120992
- DOI
- 10.3390/molecules23092351
- Appears in Collections:
- KIST Article > 2018
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