ArticleThe Journal of organic chemistry2011
Stereocontrolled total syntheses of isodomoic acids G and H via a unified strategy.
Article in The Journal of organic chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Article
- Copper catalyzed Shono-type oxidation of proline residues in peptide.Science advances · 2023Article
- Total synthesis of synechoxanthin through iterative cross-coupling.Angewandte Chemie (International ed. in English) · 2011Article
- Why You Really Should Consider Using Palladium-Catalyzed Cross-Coupling of Silanols and Silanolates.Organic process research & developmentArticle
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Authors and funding
3 authors.
Funding
Abstract
Marine neuroexcitatory compounds isodomoic acids G and H were efficiently synthesized from a common intermediate using a silicon-based cross-coupling reaction. Dividing each target compound into the core fragment and the side-chain fragment enabled the synthesis to be convergent. The trans-2,3-disubstituted pyrrolidine core fragment was accessed through a diastereoselective rhodium-catalyzed carbonylative silylcarbocyclization reaction of a vinylglycine-derived 1,6-enyne. A stereochemically divergent desilylative iodination reaction was developed to convert the cyclization product to both E- and Z-alkenyl iodides, which would eventually lead to isodomoic acid G and isodomoic acid H, respectively. The late-stage alkenyl-alkenyl silicon-based cross-coupling reaction uniting the core alkenyl iodides and the side-chain alkenylsilanol was achieved under mild conditions. Finally, two mild deprotections afforded the target molecules.
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