67217-85-0

Usage

InChI:InChI=1/C15H29N/c1-3-5-8-14-11-12-15-10-6-9-13(7-4-2)16(14)15/h13-15H,3-12H2,1-2H3/t13-,14-,15-/m1/s1

Upstream product

• 72049-65-1 (3R,8aR)-3-Butyl-5-propyl-3,5,6,7,8,8a-hexahydro-indolizine 
• 143679-77-0 (2R,6R)-(-)-2-((3S)-3-hydroxy-1-heptyl)-6-(1-propyl)-piperidine 
• 142841-61-0 (2R,5R)-N-<(benzyloxy)carbonyl>-5-butyl-2-(4-oxoheptyl)pyrrolidine 
• 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 
• 98-79-3 L-Pyroglutamic acid 
• 344749-95-7 3-triethylsilylhept-1-ene-4-ol 
• 54313-25-6 4-penten-1-yllithium 
• 5211-23-4 N-carbobenzyloxy-L-proline methyl ester 
• 214072-10-3 (5S)-2-Methoxy-1-[(benzyloxy)carbonyl]-5-methoxycarbonylpyrrolidine 
• 1119-51-3 bromopentene 
• 142841-60-9 (2R,5R)-N-<(benzyloxy)carbonyl>-2-(4-hydroxyheptyl)-5-butylpyrrolidine 

Relevant academic research and scientific papers

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.

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.

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

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

Synthesis of indolizidines (-)-195B, (-)-223AB and (-)-239AB: (2S,5R)- l-[(benzyloxy)carbonyl]-2-methoxycarbonyl-5-(4pentenyl)pyrrolidine as a versatile chiral building block

The total syntheses of three levogyre 3,5-disubstituted indolizidines, (-)-195B, (-)-223AB and (-)-239AB are described. The employed strategy is based on the utilization of the common enantiopure trans 2,5-disubstituted pyrrolidine 3, which is assembled b

Bicyclo[3.3.1]nonanes as synthetic intermediates. Part 20. Asymmetric synthesis of the indolizidine alkaloids monomorine I and indolizidine 223AB

Total syntheses of the indolizidine alkaloids monomorine I and indolizidine 223AB have been achieved by starting from the chiral cis-2,5-disubstituted pyrrolidine or cis-2,6-disubstituted piperidine obtained from the asymmetric cleavage of 8-azabicyclo[3.2.1]octan-3-one or 9-azabicyclo[3.3.1]nonan-3-one at the 'fork head'.

One-pot preparation of quinolizidin-2-one and indolizidin-7-one ring systems. Concise total synthesis of (±)-myrtine, (±)-lasubine II, and (-)-indolizidine 223AB

A highly efficient approach to the quinolizidine alkaloids (±)-myrtine (4) and (±)-lasubine II (5) and to the indolizidine alkaloid (-)-indolizidine 223AB (6) is described. The preparation of quinolizidin-2-ones 4/4a and 11b/12b and indolizidin-7-ones 16/