A formal synthesis of (−)-swainsonine from a chiral aziridine

Choi, Hwan Geun; Kwon, Ji Hye; Kim, Jong Chan; Lee, Won Koo; Eum, Heesung; Ha, Hyun‐Joon

doi:10.1016/j.tetlet.2010.04.069

Cited by 28 publications

(9 citation statements)

References 24 publications

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“…A formal synthesis of enantiomerically pure (−)‐swainsonine was successfully achieved by the formation of (2 S ,3 R )‐2‐vinyl‐3‐hydroxypiperidine 54 , which was derived from (2 S ,3 R )‐2‐hydroxymethyl‐3‐hydroxypiperidine 53 , as shown in Scheme 35. The Weinreb amide 8 was treated with magnesium and commercially available (3‐bromopropoxy)‐ tert ‐butyldimethylsilane in THF to provide the corresponding ketone 50 in 67 % yield.…”

Section: Application Of Chiral Aziridine‐2‐carboxylatesmentioning

confidence: 99%

Application of Regio‐ and Stereoselective Functional Group Transformations of Chiral Aziridine‐2‐carboxylates

Jung

Lee

2014

Asian J Org Chem

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Chiral aziridine-2-carboxylates have two important functional groups, the carboxylate group and aziridine ring, that are useful for synthetic purposes. As both (2R)-and (2S)-aziridine-2-carboxylates were commercialized in optically pure forms, we have studied to extend their synthetic utilities for the construction of various nitrogen-containing molecules. The C2 ester group can be transformed into aldehydes, alcohols, amides, ketones, b-ketoesters, and amines bearing diverse substituents with defined stereochemistry in high yields. In particular, ring-opening reactions of aziridines are carried out in regio-and stereoselective manners toward a-or b-amino cyclic and acyclic compounds in optically pure forms. The highlight of this chemistry based on the regio-and stereoselective functional-group transformations of aziridine-2-carboxylates is exemplified by efficient and highly stereoselective syntheses of many biologically important amines, including natural products.

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Section: Application Of Chiral Aziridine‐2‐carboxylatesmentioning

confidence: 99%

Application of Regio‐ and Stereoselective Functional Group Transformations of Chiral Aziridine‐2‐carboxylates

Jung

Lee

2014

Asian J Org Chem

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“…Mg (819 mg, 34.14 mmol) was added to a stirring solution of ( R )‐ N ‐methoxy‐ N ‐methyl‐1‐[( R )‐1‐phenylethyl]aziridine‐2‐carboxamide (2.0 g, 8.53 mmol) and (3‐bromopropoxy)( tert ‐butyl)dimethylsilane (3.97 mL, 17.07 mmol) in anhydrous THF (10 mL) at RT. The reaction was heated to reflux, 1,2‐dibromoethane was added, and the mixture was stirred at reflux (80 °C) for a further 4 h. Then, the reaction was cooled to RT, quenched with a saturated aqueous solution of NH 4 Cl, and extracted with EtOAc (3×50 mL).…”

Section: Methodsmentioning

confidence: 99%

“…The procedure was analogous to that used for the preparation of compound 40 by using compound 44 (400 mg, 1.15 mmol), ZnCl 2 (234 mg, 1.72 mmol), and NaBH 4 (87 mg, 2.29 mmol) to afford compound 45 (390 mg, 97 % yield).…”

Section: Methodsmentioning

confidence: 99%

Preparation of a Stable Bicyclic Aziridinium Ion and Its Ring Expansion toward Piperidines and Azepanes

Choi

Yadav

2017

Asian J Org Chem

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The formation of the stable form of 1-azabicyclo[4.1.0]heptane tosylate was successfully achieved from 2-[4-tolenesulfonyloxybutyl]aziridine, by stirring in MeCNa t room temperature. The ring strain in the three-membered ring could be released through the cleavageo fe ither CÀN bond, but ring opening with various nucleophilesproceeded in ah ighly regio-ands tereoselective manner.T wo possible pathways, in which the aziridine ringw as opened by nucleophilic attack at the bridge and the bridgehead, yielded piperidine and azepane rings, respectively.T his selective transformation starting from chiral aziridines constitutes an efficient route for the asymmetric synthesis of biologically importantn atural products, such as fagomines,f ebrifugine, sedamine, hydroxypipecolic acid, and balanol.

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“…The latter amine 9 was then transformed into piperidine 10 via cyclization between nitrogen and C6, which served as a synthetic substrate for the preparation of (-)-swainsonine (11; Scheme 3). 14 The indolizidine alkaloid (-)-swainsonine (11), which is known to be a potent inhibitor of Golgi -mannosidase II, was first isolated from the fungus of Rhizoctonia leguminicola. 15…”

Section: Scheme 2 Total Synthesis Of (-)-8-epi-swainsoninementioning

confidence: 99%

Deployment of Aziridines for the Synthesis of Alkaloids and Their Derivatives

Macha

D’hooghe

2019

Synthesis

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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

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A formal synthesis of (−)-swainsonine from a chiral aziridine

Cited by 28 publications

References 24 publications

Application of Regio‐ and Stereoselective Functional Group Transformations of Chiral Aziridine‐2‐carboxylates

Application of Regio‐ and Stereoselective Functional Group Transformations of Chiral Aziridine‐2‐carboxylates

Preparation of a Stable Bicyclic Aziridinium Ion and Its Ring Expansion toward Piperidines and Azepanes

Deployment of Aziridines for the Synthesis of Alkaloids and Their Derivatives

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