NDLI: Enantiopure 2,6-disubstituted piperidines bearing one alkene- or alkyne-containing substituent: preparation and application to total syntheses of indolizidine-alkaloids

Please wait, while we are loading the content...

A comparative study of the self-immolation of para-aminobenzylalcohol and hemithioaminal-based linkers in the context of protease-sensitive fluorogenic probes

Enantioselective assembly of the benzo[d]xanthene tetracyclic core of anti-influenza active natural products

Pestalactams A–C: novel caprolactams from the endophytic fungus Pestalotiopsis sp.

Antimicrobially active cycloundecapeptides related to gramicidin S having a novel turn structure with cisd-Phe-Pro peptide bond

The application of flow microreactors to the preparation of a family of casein kinase I inhibitors

Locked chromophores as CD and NMR probes for the helical conformation of tetraamidic macrocycles

Zn(OTf)₂-catalyzed addition of amines to carbodiimides: efficient synthesis of guanidines and unpredicted formation of Zn–N amido species

Synthesis of NH006—a photostable fungicide effective against Botrytis cinerea—according to the asymmetric total synthesis of MK8383

Nitroreductase from Salmonella typhimurium: characterization and catalytic activity

Synthesis of the first spacer containing prodrug of a duocarmycin analogue and determination of its biological activity

Novel nucleobase-simplified cyclic ADP-ribose analogue: A concise synthesis and Ca²⁺-mobilizing activity in T-lymphocytes

Comparative studies on lectin–carbohydrate interactions in low and high density homo- and heteroglycoclusters

Streptococcus pneumoniae endohexosaminidase D; feasibility of using N-glycan oxazoline donors for synthetic glycosylation of a GlcNAc-asparagine acceptor

Electron transfer from aromatic amino acids to guanine and adenine radical cations in π stacked and T-shaped complexes

Structure elucidation and spectroscopic analysis of photodegradants of the anti-rhinitis drug fluticasone furoate

Oligoproline helices as structurally defined scaffolds for oligomeric G protein-coupled receptor ligands

Proteasome selectivity towards Michael acceptor containing oligopeptide-based inhibitors

Synthesis of spirocyclic carbazole- and acridine-lactams

Enantiopure 2,6-disubstituted piperidines bearing one alkene- or alkyne-containing substituent: preparation and application to total syntheses of indolizidine-alkaloids

Synthesis of the structure proposed for the natural allenic antibiotic scorodonin

Novel polycarboxylated EDTA-type cyclodextrins as ligands for lanthanide binding: study of their luminescence, relaxivity properties of Gd(iii) complexes, and PM3 theoretical calculations

Atropisomeric 8-arylchromen-4-ones exhibit enantioselective inhibition of the DNA-dependent protein kinase (DNA-PK)

Nucleophilicities and Lewis basicities of imidazoles, benzimidazoles, and benzotriazoles

Versatile microwave-induced reactions for the multiple functionalization of carbon nanotubes

A thermodynamic study of selective solvation in solvent mixtures

Syntheses, structures, modification, and optical properties of meso-tetraaryl-2,3-dimethoxychlorin, and two isomeric meso-tetraaryl-2,3,12,13-tetrahydroxybacteriochlorins

Chemical synthesis of mouse pro-opiomelanocortin(1–74) by azido-protected glycopeptide ligation via the thioester method

Back matter

Back cover

Organic & Biomolecular Chemistry Vol - 8 Issue - 7

Organic & Biomolecular Chemistry Vol - 8 Issue - 6

Organic & Biomolecular Chemistry Vol - 8 Issue - 5

Organic & Biomolecular Chemistry Vol - 8 Issue - 4

Organic & Biomolecular Chemistry Vol - 8 Issue - 3

Organic & Biomolecular Chemistry Vol -7

Organic & Biomolecular Chemistry Vol -6

Organic & Biomolecular Chemistry Vol -5

Organic & Biomolecular Chemistry Vol -4

Organic & Biomolecular Chemistry Vol -3

Organic & Biomolecular Chemistry Vol -2

Enantiopure 2,6-disubstituted piperidines bearing one alkene- or alkyne-containing substituent: preparation and application to total syntheses of indolizidine-alkaloids

Content Provider	Royal Society of Chemistry (RSC)
Author	Cheng, Guolin Xu, Jimin Su, Deyong Liu, Hui Hu, Yuefei Wang, Xinyan
Copyright Year	2010
Abstract	A general and efficient procedure for the preparation of 2,6-disubstituted piperidines bearing one alkene- or alkyne-containing substituent was developed by using non-racemic Betti base as a chiral auxiliary. Many chiral benzylamines are excellent auxiliaries, but they were rarely used for this purpose because of the inefficient removal of the N-benzyl auxiliary residue under non-hydrogenative conditions. We found that N,N-disubstituted Betti base derivative has a typical Mannich structure of o-naphthol. When it carried out a base-catalyzed formation of o-quinone methide, an efficient non-hydrogenative N-debenzylation was achieved, and the alkene and alkyne groups survived. To demonstrate the efficiency of the method and the versatility of the products, asymmetric total syntheses of indolizidine-alkaloids (−)-167B, (−)-195H, (−)-209D and (−)-223AB were accomplished.
Starting Page	1899
Ending Page	1904
Page Count	6
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	8
Issue Number	8
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b927007h
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Chiral auxiliary Alkene Enantiomer Betti Substituent Piperidine Total synthesis Alkyne
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

Sl.	Authority	Responsibilities	Communication Details
1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
2	Indian Institute of Technology Kharagpur	Host Institute of the Project: The host institute of the project is responsible for providing infrastructure support and hosting the project	https://www.iitkgp.ac.in
3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
5	Website/Portal (Helpdesk)	Queries regarding NDLI and its services	support@ndl.gov.in
6	Contents and Copyright Issues	Queries related to content curation and copyright issues	content@ndl.gov.in
7	National Digital Library of India Club (NDLI Club)	Queries related to NDLI Club formation, support, user awareness program, seminar/symposium, collaboration, social media, promotion, and outreach	clubsupport@ndl.gov.in
8	Digital Preservation Centre (DPC)	Assistance with digitizing and archiving copyright-free printed books	dpc@ndl.gov.in
9	IDR Setup or Support	Queries related to establishment and support of Institutional Digital Repository (IDR) and IDR workshops	idr@ndl.gov.in

Preparation of enantiopure substituted piperidines containing 2-alkene or 2-alkyne chains: application to total syntheses of natural quinolizidine-alkaloids.

Cross-Metathesis of Chiral N-tert-Butylsulfinyl Homoallylamines: Application to the Enantioselective Synthesis of Naturally Occurring 2,6-cis-Disubstituted Piperidines

Stereoselective Synthesis of 2,6-Disubstituted Piperidines Using the Iridium-Catalyzed Allylic Cyclization as Configurational Switch: Asymmetric Total Synthesis of (+)-241 D and Related Piperidine Alkaloids

Enantioselective Syntheses of 2-Alkyl-, 2,6-Dialkylpiperidines and Indolizidine Alkaloids Through Diastereoselective Mannich-Michael Reactions

One-pot multiple reactions: asymmetric synthesis of 2,6-cis-disubstituted piperidine alkaloids from chiral aziridine.

Diastereoselective preparation of cyclic β-aminoketals. Application to the total synthesis of piperidine alkaloids

Formal Syntheses of 5,8-Disubstituted Indolizidine Alkaloids (–)-205A, (–)-207A, and (–)-235B

Total synthesis of (5R,6R,8R,9S)-(−)-5,9Z-indolizidine 221T using sulfinimine-derived N-sulfinyl β-amino ketones

Efficient stereoselective syntheses of piperidine, pyrrolidine, and indolizidine alkaloids

Enantiopure 2,6-disubstituted piperidines bearing one alkene- or alkyne-containing substituent: preparation and application to total syntheses of indolizidine-alkaloids

Similar Documents

Preparation of enantiopure substituted piperidines containing 2-alkene or 2-alkyne chains: application to total syntheses of natural quinolizidine-alkaloids.

Cross-Metathesis of Chiral N-tert-Butylsulfinyl Homoallylamines: Application to the Enantioselective Synthesis of Naturally Occurring 2,6-cis-Disubstituted Piperidines

Stereoselective Synthesis of 2,6-Disubstituted Piperidines Using the Iridium-Catalyzed Allylic Cyclization as Configurational Switch: Asymmetric Total Synthesis of (+)-241 D and Related Piperidine Alkaloids

Enantioselective Syntheses of 2-Alkyl-, 2,6-Dialkylpiperidines and Indolizidine Alkaloids Through Diastereoselective Mannich-Michael Reactions

One-pot multiple reactions: asymmetric synthesis of 2,6-cis-disubstituted piperidine alkaloids from chiral aziridine.

Diastereoselective preparation of cyclic β-aminoketals. Application to the total synthesis of piperidine alkaloids

Formal Syntheses of 5,8-Disubstituted Indolizidine Alkaloids (–)-205A, (–)-207A, and (–)-235B

Total synthesis of (5R,6R,8R,9S)-(−)-5,9Z-indolizidine 221T using sulfinimine-derived N-sulfinyl β-amino ketones

Efficient stereoselective syntheses of piperidine, pyrrolidine, and indolizidine alkaloids

Enantiopure 2,6-disubstituted piperidines bearing one alkene- or alkyne-containing substituent: preparation and application to total syntheses of indolizidine-alkaloids