72120-43-5

Upstream product

• 105281-77-4 (5R,8aR)-3-(1-Chloro-butyl)-5-propyl-octahydro-indolizine 
• 118311-69-6 (3S,5R,8aR)-3-(2-Ethyl-[1,3]dithiolan-2-ylmethyl)-5-propyl-octahydro-indolizine; hydrochloride 
• 120153-68-6 N-benzylpiperidine-2-carbonitrile 
• 98195-27-8 1-benzyl-2-n-propylpiperidine 
• 83024-09-3 2-ethyl-2-nonan-9-yl>-1,3-dithiacyclohexane 
• 111-30-8 Glutaraldehyde 
• 82979-20-2 2-ethyl-2-nonan-9-yl>-1,3-dithiacyclohexane 
• 191665-91-5 (3S,5R,8aR)-3-(1-Chloro-butyl)-5-propyl-octahydro-indolizine 
• 692730-61-3 (-)-(3'R,5'R,8'aS)-3'-butylhexahydro-5-propylspiro[1,3-dithiane-2,7'-(1'H)indolizine] 
• 15681-48-8 dimethyllithium cuprate 
• 292615-27-1 Toluene-4-sulfonic acid 2-((3R,5S,8aR)-3-butyl-octahydro-indolizin-5-yl)-ethyl ester 
• 2100-17-6 4-pentenal 
• 54313-25-6 4-penten-1-yllithium 
• 158149-95-2 (2S,5R)-1-[(Benzyloxy)carbonyl]-2-methoxycarbonyl-5-(pent-4-enyl)pyrrolidine 

Relevant academic research and scientific papers

Enantioselective addition of activated terminal alkynes to 1-acylpyridinium salts catalyzed by Cu-Bis(oxazoline) complexes

CuI/bis(oxazoline)-catalyzed addition of propiolates and terminal ynones to 1-acylpyridinium salt (generated in situ from reaction of pyridine and methyl chloroformate) affords highly functionalized dihydropyridines with excellent enantioselectivity. It is found that the carbonyl group adjacent to the alkyne moiety is essential for the enantioselectivity of the addition. Short synthesis of indolizidines 167B and 223AB is achieved by employing two addition products. Copyright

C-H Functionalization of Amino Alcohols by Osmium Tetroxide/NMO or TPAP/NMO: Protecting Group-Free Synthesis of Indolizidines (–)-223AB and 3-epi-(–)-223AB

The oxidative cyclization of amino alcohols by osmium tetroxide/NMO or tetrapropylammonium perruthenate (TPAP)/NMO was found to provide an N,O-acetal moiety through the trapping of the resulting iminium ion by the alcohol. These two transformations were demonstrated in the synthesis of indolizidines (–)-223AB and 3-epi-(–)-223AB.

A short and modular approach towards 3,5-disubstituted indolizidine alkaloids

3,5-Dialkyl indolizidines have been prepared in four linear steps from commercially available starting materials. The sequence involves two direct α-functionalization steps and a subsequent reductive amination and provides diastereoselective access to both C-3 epimers of the 5,9-trans-substituted indolizines. The naturally occurring indolizidines 195B and 223AB have been synthesized using this methodology.

Cross-coupling of cyclopropanols: Concise syntheses of indolizidine 223AB and congeners

A new synthetic method for indolizidine or pyrrolizidine alkaloids based on readily available and attractively functionalized cyclopropanols, as exemplified in concise syntheses of indolizidine (-)-223AB, its 3-epimer, (-)-indolizidine 239AB, and (-)-indolizidine 239CD, is reported. This work highlights the applications of SN2′ alkylation and C-acylation of cyclopropanols to meet stereochemical challenges in natural product synthesis. Also included is diastereoselective cyclization of the resulting aminoallene adduct for bicyclic ring formation.

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

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.

Asymmetric synthesis of 3,5-disubstituted indolizidines by intermolecular addition of an allylsilane on an N-acyliminium ion

A diastereoselective synthesis of 3,5-disubstituted indolizidines based on an intermolecular addition of an allylsilane on an acyliminium ion derived from (S)-pyroglutamic acid is described. The synthetic potential of this methodology is demonstrated by t

A general, convergent strategy for the construction of indolizidine alkaloids: Total syntheses of (-)-indolizidine 223AB and alkaloid (-)-205B

N-Toluenesulfonyl aziridines comprise effective second electrophiles in the solvent controlled three-component linchpin union of silyl dithianes for the stereocontrolled convergent elaboration of protected 1,5-amino alcohols. This tactic, in conjunction w

Multicomponent linchpin coupling of silyl dithianes employing an N-Ts aziridine as the second electrophile: Synthesis of (-)-indolizidine 223AB

An efficient, stereocontrolled assembly of the indolizidine alkaloid, (-)-indolizidine 223AB, exploiting a three-component linchpin coupling employing an N-Ts aziridine as the second electrophile, followed by a one-pot sequential construction of the indol

Reversal of diastereofacial selectivity in the nucleophilic addition reaction to chiral N-sulfinimine and application to the synthesis of indrizidine 223AB

Diastereoselective addition reaction of ester enolates and Grignard reagents to optically active N-sulfinimines was examined. Reversal of the diastereofacial selectivity was realized by using appropriate metal species, solvents and additives, and the β-amino esters (up to >98% de) and the homoallylic amines (up to >98% de) were obtained in good yields. β-Amino esters thus obtained were converted to the useful β-amino acids involving (R)-homoserine. Application to the synthesis of indrizidine alkaloids was also described.

Radical cyclization of beta-aminoacrylates: synthesis of (-)-indolizidine 223AB.

[reaction: see text] (-)-Indolizidine 223AB was synthesized via radical cyclization of the beta-aminoacrylate derivative of a trans-2,5-disubstituted pyrrolidine. The trans-2,5-disubstituted pyrrolidine substrate was prepared by radical cyclization of a S