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- Title
Divergent Syntheses of (-)-Chicanine, (+)-Fragransin A 2 , (+)-Galbelgin, (+)-Talaumidin, and (+)-Galbacin via One-Pot Homologative γ -Butyrolactonization.
- Authors
Choi, Hosam; Han, Jongyeol; Choi, Joohee; Lee, Kiyoun
- Abstract
In this study, the divergent syntheses of (-)-chicanine, (+)-fragransin A2, (+)-galbelgin, (+)-talaumidin, and (+)-galbacin are detailed. In this approach, an early-stage modified Kowalski one-carbon homologation reaction is utilized to construct the central γ-butyrolactone framework with the two necessary β,γ-vicinal stereogenic centers. The two common chiral γ-butyrolactone intermediates were designed to be capable for assembling five different optically active tetrahydrofuran lignans from commercially available materials in a concise and effective divergent manner in five to eight steps. These five syntheses are among the shortest and highest-yielding syntheses reported to date.
- Subjects
LIGNANS; TETRAHYDROFURAN
- Publication
Molecules, 2024, Vol 29, Issue 3, p701
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules29030701