Stereoselective synthesis of (−)-8-epi-swainsonine starting with a chiral aziridine

Lee, Baeck Kyoung; Choi, Hwan Geun; Roh, Eun Joo; Lee, Won Koo; Sim, Taebo

doi:10.1016/j.tetlet.2012.11.087

Cited by 18 publications

(24 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In close analogy, an efficient synthesis of (-)-8-episwainsonine (7) has been established from commercial 1-(R)--methylbenzylaziridine-2-methanol (1b), which was converted into pyrrolidinone 6 as a precursor for the preparation of (-)-8-epi-swainsonine (7; Scheme 2). 13…”

Section: Review Syn Thesismentioning

confidence: 99%

Deployment of Aziridines for the Synthesis of Alkaloids and Their Derivatives

Macha

D’hooghe

2019

Synthesis

View full text Add to dashboard Cite

Various (activated and non-activated) aziridines with diverse substitution patterns have been deployed successfully as starting materials for the synthesis of a wide variety of alkaloids via suitable functionalization and aziridine ring transformation. Alternatively, the preparation and interception of reactive aziridine intermediates has also been shown to constitute a valid approach toward alkaloid synthesis. This review summarizes aziridine-mediated syntheses of alkaloids, in which the aziridine is mobilized as either a substrate or an advanced synthetic intermediate.1 Introduction2 Alkaloids Synthesis from Aziridine Starting Materials2.1 (2R)- and (2S)-Hydroxymethyl-N-(1-phenylethyl)aziridines2.2 N-Benzylaziridine-2-carboxylates2.3 2-Substituted N-Tosyl- or N-Tritylaziridines2.4 2,3-Disubstituted N-Cbz- or N-Tosylaziridines2.5 N-DMB-aziridines3 Alkaloids Synthesis from Aziridines as Key Advanced Synthetic Intermediates3.1 Alkylative Aziridine Ring Opening3.2 Arylative Aziridine Ring Opening3.3 Ring Expansion3.4 Oxidative Aziridine Ring Opening3.5 Heteroatomic Nucleophilic Aziridine Ring Opening3.6 Reductive Aziridine Ring Opening4 Conclusion

show abstract

Section: Review Syn Thesismentioning

confidence: 99%

Deployment of Aziridines for the Synthesis of Alkaloids and Their Derivatives

Macha

D’hooghe

2019

Synthesis

View full text Add to dashboard Cite

show abstract

“…The elegant approach to 8- epi -swainsonine ((1 S ,2 R ,8 S ,8a R )- 231 ) started from cis -acrylate (2 S ,1' R )- 156a readily separable from a 4:1 cis : trans mixture prepared in Wittig reaction from the aldehyde (2 R ,1' R )- 6 (Scheme 58) [120]. Sharpless asymmetric dihydroxylation of (2 S ,1' R )- 156a provided a 10:1 mixture of diols with the diastereoisomer 232 predominating.…”

Section: Reviewmentioning

confidence: 99%

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

Głowacka¹,

Trocha²,

Wróblewski³

et al. 2019

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

Since Garner’s aldehyde has several drawbacks, first of all is prone to racemization, alternative three-carbon chirons would be of great value in enantioselective syntheses of natural compounds and/or drugs. This review article summarizes applications of N-(1-phenylethyl)aziridine-2-carboxylates, -carbaldehydes and -methanols in syntheses of approved drugs and potential medications as well as of natural products mostly alkaloids but also sphingoids and ceramides and their 1- and 3-deoxy analogues and several hydroxy amino acids and their precursors. Designed strategies provided new procedures to several drugs and alternative approaches to natural products and proved efficiency of a 2-substituted N-(1-phenylethyl)aziridine framework as chiron bearing a chiral auxiliary.

show abstract

“…Indolizine, an important class of heterocycles, has attracted critical attention of chemists for its application value. They are found in a large number of natural products such as (±)-homocrepidine A (Hu et al, 2015), tashiromine (Marsden and McElhinney, 2008), swainsonine (Lee et al, 2013), Pandalisines A and B (Cheng et al, 2015), Flueggedine (Zhao et al, 2013), and so on. Recent studies have indicated that indolizines exhibit a broad range of biological activities including anti-herpesvirus (De Bolle et al, 2004), cyclooxygenase and lipoxygenase inhibition (Shrivastava et al, 2017), inhibition of Mycobacterium tuberculosis (Gundersen et al, 2007), and Ach receptor agonist (Xue et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

A Novel Indolizine Derivative Induces Apoptosis Through the Mitochondria p53 Pathway in HepG2 Cells

et al. 2019

View full text Add to dashboard Cite

Indolizine derivatives are a class of compounds with excellent biological activity. In this study, a series of indolizine derivatives, compound 1 (C1), compound 2 (C2), compound 3 (C3), and compound 4 (C4), were synthesized. 3-(4,5-dimethylthiazole)-2,5-diphenyltetraazolium bromide (MTT) assay was used to evaluate their cytotoxicity against HepG2 (p53-wild), A549, and HeLa cell lines. HepG2 cells apoptosis induced by C3 was determined using Hoechst staining and acridine orange/ethidium bromide staining. Cells’ apoptotic ratio was measured by Annexin V–FITC/PI double staining. Changes in mitochondrial membrane potential and intracellular reactive oxygen species (ROS) in HepG2 cells after C3 treatment were determined. Immunofluorescence staining and Western blot analysis were carried out to detect p53 levels and analyze the apoptosis-associated proteins, respectively. Moreover, the cytotoxic activity of C3 was examined in two other hepatocellular carcinoma (HCC) cell lines with different p53 status including Huh-7 cells (p53-mutant) and Hep3B cells (p53-null). The results indicated that C3 showed stronger inhibition towards HepG2 cells than other cell lines. Fluorescent staining and flow cytometry analysis confirmed that C3 induced apoptosis of HepG2 cells. C3 could also increase intracellular ROS and cause a decrease in the mitochondrial membrane potential. C3 promoted p53 activation and increased p53 accumulation in nuclei. The expression of p53 and Bax was increased with the down-regulation of Bcl-2, which promoted the release of cytochrome c and caspase-3 activation. Collectively, the study demonstrated that C3 caused HepG2 cell apoptosis via the mitochondria p53 pathway. These results inspired us to further develop indolizine derivatives as potential potent inhibitors against liver cancer.

show abstract

Stereoselective synthesis of (−)-8-epi-swainsonine starting with a chiral aziridine

Cited by 18 publications

References 33 publications

Deployment of Aziridines for the Synthesis of Alkaloids and Their Derivatives

Deployment of Aziridines for the Synthesis of Alkaloids and Their Derivatives

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

A Novel Indolizine Derivative Induces Apoptosis Through the Mitochondria p53 Pathway in HepG2 Cells

Contact Info

Product

Resources

About