ArticleJournal of the American Chemical Society2009
Total syntheses of isodomoic acids G and H: an exercise in tetrasubstituted alkene synthesis.
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 8 papers.
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Who cites it
8 citing papers in PubMed, 50 citations in OpenAlex.
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- Metallacycle-Mediated Cross-Coupling in Natural Product Synthesis.Tetrahedron · 2016Article
- Scope and Mechanistic Study of the Coupling Reaction of α, β-Unsaturated Carbonyl Compounds with Alkenes: Uncovering Electronic Effects on Alkene Insertion vs Oxidative Coupling Pathways.Organometallics · 2012Article
- Nickel-catalyzed cyclizations of enoates and chiral allenes: an approach to domoic acid.Chemistry (Weinheim an der Bergstrasse, Germany) · 2011Article
- Tetrasubstituted olefins through the stereoselective catalytic intermolecular conjugate addition of simple alkenes to α,β-unsaturated carbonyl compounds.Angewandte Chemie (International ed. in English) · 2011Article
- Stereocontrolled total syntheses of isodomoic acids G and H via a unified strategy.The Journal of organic chemistry · 2011Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
A unified approach to the pyrrolidine triacid natural products isodomoic acids G and H has been developed. Total syntheses of both natural products were completed, and determination of the correct stereostructure of isodomoic acid G was established by comparing 5'-(R) and 5'-(S) isomers to a sample of authentic material. A nickel-catalyzed cyclization constructs the pyrrolidine ring while simultaneously establishing either the E or Z stereochemistry of an exocyclic tetrasubstituted alkene. Stereoselective assembly of both the E- and Z-alkenes of the natural products is made possible by a predictable strategy that alters the timing of substituent introduction to control alkene stereochemistry.
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