ArticleJournal of the American Chemical Society2009
Total syntheses of isodomoic acids G and H.
Article in Journal of the American Chemical Society, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- The Chemistry of Phytoplankton.Chemical reviews · 2024Review
- Enantioselective synthesis of α-alkenyl α-amino acidsChemical science · 2016Article
- Regioselective allene hydroarylation via one-pot allene hydrosilylation/Pd-catalyzed cross-coupling.Organic letters · 2014Article
- Total synthesis of synechoxanthin through iterative cross-coupling.Angewandte Chemie (International ed. in English) · 2011Article
- Nickel-catalyzed cyclizations of enoates and chiral allenes: an approach to domoic acid.Chemistry (Weinheim an der Bergstrasse, Germany) · 2011Article
- Stereocontrolled total syntheses of isodomoic acids G and H via a unified strategy.The Journal of organic chemistry · 2011Article
- Sequential Processes in Palladium-Catalyzed Silicon-Based Cross-Coupling.Israel journal of chemistry · 2010Article
- Development of a general, sequential, ring-closing metathesis/intramolecular cross-coupling reaction for the synthesis of polyunsaturated macrolactones.Journal of the American Chemical Society · 2010Article
- Silicon-based cross-coupling reactions in the total synthesis of natural products.Angewandte Chemie (International ed. in English) · 2010Review
- Total syntheses of isodomoic acids G and H: an exercise in tetrasubstituted alkene synthesis.Journal of the American Chemical Society · 2009Article
- Why You Really Should Consider Using Palladium-Catalyzed Cross-Coupling of Silanols and Silanolates.Organic process research & developmentArticle
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3 authors.
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Abstract
The total syntheses of marine natural products belonging to the kainoid family, isodomoic acids G and H, are described. The strategic connection involves a sequential silylcarbocyclization/silicon-based cross-coupling process. These total syntheses were achieved efficiently via a 12- and a 13-step, longest-linear sequence, respectively. The key transformations include a diastereoselective rhodium-catalyzed carbonylative silylcarbocyclization reaction of an (l)-vinylglycine-derived 1,6-enyne, a desilylative iodination reaction, as well as an alkenyl-alkenyl silicon-based cross-coupling reaction. The mechanistic insight garnered during the investigation of the iododesilylation reaction enabled stereocontrolled introduction of the iodine with either inversion or retention of double bond configuration. The invertive desilylative iodination leads to the total synthesis of isodomoic acid H, while its congener, isodomoic acid G, was obtained via a retentive iododesilylation.
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