ArticleJournal of the American Chemical Society2012
Synthesis of alkaloid (-)-205B via stereoselective reductive cross-coupling and intramolecular [3+2] cycloaddition.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 40 citations in OpenAlex.
- Total synthesis of the natural (-)-205B alkaloid and its activity toward α7 nAChRs.Organic & biomolecular chemistry · 2023Article
- Enantioselective Aza-Sakurai Cyclizations: Dual Role of Thiourea as H-Bond Donor and Lewis Base.Journal of the American Chemical Society · 2016Article
- Metallacycle-Mediated Cross-Coupling in Natural Product Synthesis.Tetrahedron · 2016Article
- Regio- and Diastereoselective Synthesis of Highly Substituted, Oxygenated Piperidines from Tetrahydropyridines.The Journal of organic chemistry · 2015Article
- Total synthesis of alkaloid 205B.The Journal of organic chemistry · 2014Article
- Convergent Synthesis of Diverse Tetrahydropyridines via Rh(I)-Catalyzed C-H Functionalization Sequences.Organic process research & development · 2014Review
- Regio- and stereoselective 1,2-dihydropyridine alkylation/addition sequence for the synthesis of piperidines with quaternary centers.Angewandte Chemie (International ed. in English) · 2014Article
- Stereochemical lability of azatitanacyclopropanes: dynamic kinetic resolution in reductive cross-coupling reactions with allylic alcohols.Chemical communications (Cambridge, England) · 2013Article
- Catalytic Z-selective cross-metathesis with secondary silyl- and benzyl-protected allylic ethers: mechanistic aspects and applications to natural product synthesis.Angewandte Chemie (International ed. in English) · 2013Article
- Titanium tales.Nature chemistry · 2013Article
- Unstabilized azomethine ylides for the stereoselective synthesis of substituted piperidines, tropanes, and azabicyclo[3.1.0] systems.Journal of the American Chemical Society · 2013Article
- A Highly Chemo-, Regio-, and Stereoselective Metallacycle-Mediated Annulation Between a Conjugated Enyne and an Ene-Diyne.ARKIVOC : free online journal of organic chemistryArticle
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2 authors at 1 institution in 1 country.
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Abstract
An asymmetric synthesis of alkaloid (-)-205B, a tricyclic member of the architecturally diverse family of natural products isolated from the skin of neotropical poison frogs, is described that proceeds through two recently developed stereoselective synthetic methods: (1) Ti-mediated allylic alcohol-imine reductive cross-coupling and (2) intramolecular [3+2] cycloaddition of a glyoxylate-based homoallylic nitrone. The utility of this latter cycloaddition process for the assembly of the stereochemically dense piperidine core of 205B is noteworthy, as this method enables direct [3+2] cycloaddition of an intermediate homoallylic (E)-nitrone via a pathway that is stereochemically unscathed by competitive [3,3]-sigmatropic rearrangement processes. Overall, the synthesis is asymmetric, concise, and highly stereoselective-features which point to the potential future utility of these chemical methods in natural product synthesis and medicinal chemistry.
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