ArticleOrganic letters2011
Nitrenium ion-mediated alkene bis-cyclofunctionalization: total synthesis of (-)-swainsonine.
Article in Organic letters, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed, 61 citations in OpenAlex.
- Photochemical generation and characterization of the 5-endo-10,11-dihydrodibenzoazepine nitrenium ion.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2022Article
- Electrophilic Aminating Agents in Total Synthesis.Angewandte Chemie (International ed. in English) · 2021Review
- The PIFA-initiated oxidative cyclization of 2-(3-butenyl)quinazolin-4(3Beilstein journal of organic chemistry · 2021Article
- Alkene Difunctionalization Using Hypervalent Iodine Reagents: Progress and Developments in the Past Ten Years.Molecules (Basel, Switzerland) · 2019Review
- Direct synthesis of imino-C-nucleoside analogues and other biologically active iminosugars.Nature communications · 2015Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
The total synthesis of (-)-swainsonine from 2,3-O-isopropylidene-D-erythrose in 12 steps and an overall yield of 28% is reported. The pivotal transformation in our route to this indolizidine alkaloid is the formation of the pyrrolidine ring and C-8a/8 stereodiad through the diastereoselective, bis-cyclofunctionalization of an γ,δ-unsaturated O-alkyl hydroxamate. This transformation is believed to proceed via the intramolecular capture of an N-acyl-N-alkoxyaziridinium ion generated by the diastereoselective addition of a singlet acylnitrenium ion to the pendant alkene.
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