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Divergent Syntheses of (-)-Chicanine, (+)-Fragransin A₂, (+)-Galbelgin, (+)-Talaumidin, and (+)-Galbacin via One-Pot Homologative γ-Butyrolactonization.

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.

SUBMITTER: Choi H

PROVIDER: S-EPMC10856021 | biostudies-literature | 2024 Feb

REPOSITORIES: biostudies-literature

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Dataset Information

Divergent Syntheses of (-)-Chicanine, (+)-Fragransin A₂, (+)-Galbelgin, (+)-Talaumidin, and (+)-Galbacin via One-Pot Homologative γ-Butyrolactonization.

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Dataset Information

Divergent Syntheses of (-)-Chicanine, (+)-Fragransin A2, (+)-Galbelgin, (+)-Talaumidin, and (+)-Galbacin via One-Pot Homologative γ-Butyrolactonization.

OmicsDI is part of the ELIXIR infrastructure

Tweets

Divergent Syntheses of (-)-Chicanine, (+)-Fragransin A₂, (+)-Galbelgin, (+)-Talaumidin, and (+)-Galbacin via One-Pot Homologative γ-Butyrolactonization.