ArticleJournal of the American Chemical Society2010
Development of a general, sequential, ring-closing metathesis/intramolecular cross-coupling reaction for the synthesis of polyunsaturated macrolactones.
Article in Journal of the American Chemical Society, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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9 citing papers in PubMed.
- A Modular, Enantioselective Synthesis of Resolvins D3, E1, and Hybrids.Organic letters · 2020Article
- Iriomoteolides: novel chemical tools to study actin dynamics.Chemical science · 2018Article
- Conditions for a Rh(I)-catalyzed [2 + 2 + 1] cycloaddition reaction with methyl substituted allenes and alkynes.Tetrahedron letters · 2015Article
- Synthesis of cyclic alkenylsiloxanes by semihydrogenation: a stereospecific route to (Z)-alkenyl polyenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2014Article
- Synthesis of oximidine II by a copper-mediated reductive ene-yne macrocyclization.Angewandte Chemie (International ed. in English) · 2011Article
- Control of olefin geometry in macrocyclic ring-closing metathesis using a removable silyl group.Journal of the American Chemical Society · 2011Article
- Formation of macrocyclic lactones in the Paternò-Büchi dimerization reaction.Beilstein journal of organic chemistry · 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
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Authors and funding
2 authors.
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Abstract
A general strategy for the construction of macrocyclic lactones containing conjugated Z,Z-1,3-diene subunits is described. The centerpiece of the strategy is a sequential ring-closing metathesis (RCM) that forms an unsaturated siloxane ring, followed by an intramolecular cross-coupling reaction with a pendant alkenyl iodide. A highly modular assembly of the various precursors allowed the preparation of unsaturated macrolactones containing 11-, 12-, 13-, and 14-membered rings. Although the RCM process proceeded uneventfully, the intramolecular cross-coupling required extensive optimization of palladium source, solvent, fluoride source, and particularly fluoride hydration level. Under the optimal conditions (including syringe pump high dilution), the macrolactones were produced in 53-78% yield as single stereoisomers. A benzo-fused 12-membered-ring macrolactone containing an E,Z-1,3-diene unit was also prepared by the same general strategy. The E-2-styryl iodide was prepared by a novel Heck reaction of an aryl nonaflate with vinyltrimethylsilane followed by iododesilylation with ICl.
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