ArticleTetrahedron2008
De Novo Asymmetric Syntheses of d-, l- and 8-epi-Swainsonine.
Article in Tetrahedron, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
5 citing papers in PubMed, 49 citations in OpenAlex.
- Stereoselective Synthesis of β-Glycinamide Ribonucleotide.Molecules (Basel, Switzerland) · 2022Article
- Synthesis and biological study of the phomopsolide and phomopsolidone natural products.Chemical communications (Cambridge, England) · 2020Review
- De novo synthesis and biological evaluation of C6″-substituted C4″-amide analogues of SL0101.Organic letters · 2014Article
- Nitrenium ion-mediated alkene bis-cyclofunctionalization: total synthesis of (-)-swainsonine.Organic letters · 2011Article
- A facile synthesis of 2-aryloxypyrimidine derivatives via a tandem reductive amination/intermolecular S(N)Ar sequence.Journal of Zhejiang University. Science. B · 2010Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
A highly enantioselective and stereocontrolled approach to d-, l- and 8-epi-d-swainsonine has been developed from achiral furan and γ-butyrolactone. A one-pot hydrogenolysis of both azide and benzyl ether followed by an intramolecular reductive amination has been employed as key step to establish the indolizidine ring system. The absolute stereochemistry was installed by the Noyori reduction and the relative stereochemistry by the use of several highly diastereoselective palladium catalyzed glycosylation, Luche reduction, dihydroxylation and palladium catalyzed azide allylation reactions. This practical approach provide multigram quantities of indolizidine natural product d-swainsonine in 13 steps and 25% overall yield.
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.