Asymmetric Synthesis of (-)-6-Desmethyl-Fluvirucinine A(1) via Conformationally-Controlled Diastereoselective Lactam-Ring Expansions

Authors
Moon, HyunyoungYoon, HojongLim, ChangjinJang, JaebongYi, Jong-JaeLee, Jae KyunLee, JeeyeonNa, YounghwaSon, Woo SungKim, Seok-HoSuh, 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
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KIST Article > 2018
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