PyrrolidineN-Oxides by Stereoselective Addition of Grignard and Lithium Compounds to 4,5-Dideoxy-2,3-O-isopropylidene-D-erythro-4-pentenoseN-Benzyl Nitrone and Subsequent Cope−House Cyclization

Palmer, Andreas Marc; Jäger, Volker

doi:10.1002/1099-0690(200104)2001:7<1293::aid-ejoc1293>3.0.co;2-4

Cited by 34 publications

(22 citation statements)

References 60 publications

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“…This is consistent with our general observation that hydroxylamine-alkyne cyclisations onto terminal and silyl-substituted acetylenes are much faster than cyclisations onto other non-terminal alkynes. 19,22 This observation is analogous to those of Ciganek 31 and Black 32 in the Cope-House cyclisation 33 of alkenyl hydroxylamines.…”

Section: Model Cyclisation Studiessupporting

confidence: 77%

“…(Z )-13-Trimethylsilyltridec-6,12-diyn-10-enoic acid 33 To a solution of 13-hydroxy-1-trimethylsilyltridec-1,7-diyn-3ene (1.0 g, 3.8 mmol) in acetone (40 cm 3 ) at Ϫ5 ЊC, was added Jones reagent (2.0 M; 7.6 cm 3 , 7.6 mmol, 2 eq.) dropwise over 10 min.…”

Section: (Z )-13-hydroxy-1-trimethylsilyltridec-17-diyn-3-enementioning

confidence: 99%

“…The aqueous solution was extracted with EtOAc (3 × 150 cm 3 ), the organic layers combined, dried (MgSO 4 ) and the solvent removed under reduced pressure. The product was purified by flash column chromatography (7 : 3 ether-hexane) to yield the acid 33 as a colourless oil (950 mg, 90%); R f 0.45 (7 : 3 (33), 243 (26), 217 (40), 189 (96), 181 (75), 175 (37), 161 (65), 157 (44) and 73 (100).…”

Section: (Z )-13-hydroxy-1-trimethylsilyltridec-17-diyn-3-enementioning

confidence: 99%

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Nitrone dipolar cycloaddition routes to piperidines and indolizidines. Part 9.Part 8. See Ref. 22. Formal synthesis of (–)-pinidine and total synthesis of (–)-histrionicotoxin, (+)-histrionicotoxin and (–)-histrionicotoxin 235AThis manuscript is dedicated to the sixtieth birthday of Professor L. Tietze.

Davison

Fox

Holmes

et al. 2002

J. Chem. Soc., Perkin Trans. 1

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Section: Model Cyclisation Studiessupporting

confidence: 77%

Section: (Z )-13-hydroxy-1-trimethylsilyltridec-17-diyn-3-enementioning

confidence: 99%

Section: (Z )-13-hydroxy-1-trimethylsilyltridec-17-diyn-3-enementioning

confidence: 99%

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Nitrone dipolar cycloaddition routes to piperidines and indolizidines. Part 9.Part 8. See Ref. 22. Formal synthesis of (–)-pinidine and total synthesis of (–)-histrionicotoxin, (+)-histrionicotoxin and (–)-histrionicotoxin 235AThis manuscript is dedicated to the sixtieth birthday of Professor L. Tietze.

Davison

Fox

Holmes

et al. 2002

J. Chem. Soc., Perkin Trans. 1

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“…Pre-complexing the nitrone with Et 2 AlCl only gives rise to modest values of syn selectivity [82]. Allylation of α-alkoxy nitrones bearing a double bond at γ-position have been used by Jager to construct homochiral pyrrolidines [83]. The use of allylmagnesium bromide affords in this case a simple isomer after the cyclization step (Scheme 56).…”

Section: Allylation Of Nitronesmentioning

confidence: 99%

Stereoselective Allylation Reactions of Imines and Related Compounds

Merino¹,

Tejero²,

Delso³

et al. 2005

COS

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The stereoselective allylation of imines and related compounds is one of the most effective methods for the introduction of an amino group into carbon skeletons. Moreover, by extending the process to other C=N functionalities such as oximes, hydrazones, nitrones and iminium ions, a variety of nitrogen-containing functional groups can be prepared with the concomitant introduction of the allyl moiety. In several instances it is possible to achieve a complete stereocontrol by using different organometallic reagents. In other cases, either the protective group tuning or the reaction time is crucial for the stereoselectivity of the reaction. This review covers the evolution of stereoselective allylation of imines and related compounds, including oximes, hydrazones, nitrones and iminium ions, from the use of allylic organometallic reagents over chiral substrates up to the recent development of enantioselective methods.

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“…起始原料为 β-内酰胺 30, 化合物 30 可由环戊二烯经过环加成反应得到 [22] . 内酰胺 30 在三乙胺和催化剂 [19] . 其中, 腺苷 A 2A 受体的激动作用可作为与呼吸系统疾病哮喘和慢性阻塞性肺病(COPD)有关的慢性炎症的治疗 [24] .…”

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Recent Progress in the Syntheses of Carbocyclic Nucleosides

Liu¹,

Guo²,

Bai³

2014

Chin. J. Org. Chem.

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Carbocyclic nucleosides are nucleoside analogues whose furanose rings are substituted by carbocycles. As analogues, many carbocyclic nucleosides show good antiviral or antitumor activities. Also, due to the absence of a typical glycosidic bond, carbocyclic nucleosides usually exhibit more metabolic stabilities to phosphorylases and hydrolases than natural nucleosides. Therefore, medicinal chemists have focused their attention on designing and preparing new carbocyclic nucleoside analogues, in efforts to discover new more powerful and safe antiviral agents. The syntheses of carbocyclic nucleosides in the past five years classified by different types of bases are reviewed in this article, denoted as purine carbocyclic nucleosides, pyrimidine carbocyclic nucleosides and carbocyclic analogues of C-nucleosides, with an emphasis on the synthesis of purine carbocyclic nucleosides. In the end, the problems and future trends of carbocyclic nucleoside research are discussed. It is still a challenge to intelligently design and efficiently synthesize the novel carbocyclic nucleosides targeted for some special purposes.

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PyrrolidineN-Oxides by Stereoselective Addition of Grignard and Lithium Compounds to 4,5-Dideoxy-2,3-O-isopropylidene-D-erythro-4-pentenoseN-Benzyl Nitrone and Subsequent Cope−House Cyclization

Cited by 34 publications

References 60 publications

Stereoselective Allylation Reactions of Imines and Related Compounds

Recent Progress in the Syntheses of Carbocyclic Nucleosides

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