26648-71-5

Usage

Uses

(-)-Halosaline is a molecule of interest because of its memory enhancing properties.

Upstream product

• 190383-62-1 [2R-(2R)]-1-benzyloxycarbonyl-2-(2-hydroxy-4-pentenyl)piperidine 
• 756821-41-7 (2R,2'R)-1-(1',2',3',6'-tetrahydropyridin-2'-yl)pent-4-en-2-ol 
• 945773-00-2 (R)-6-((R)-2-hydroxypentyl)piperidin-2-one 
• 190383-57-4 [2R-(2S)]-1-benzyloxycarbonyl-2-(2,3-epoxypropyl)piperidine 
• 60410-16-4 (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate 
• 245092-67-5 1-[1-(toluene-4-sulfonyl)-1,2,5,6-tetrahydropyridin-2-yl]pent-4-en-2-ol 
• 245092-65-3 (S)-6-((S)-2,2-Dimethyl-3,6-dihydro-2H-[1,2]oxasilin-6-ylmethyl)-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridine 
• 245092-64-2 (1S,4S)-N-[4-(allyldimethylsilanyloxy)cyclopent-2-enyl]-N-but-3-enyl-4-methylbenzene sulfonamide 
• 1257863-92-5 benzyl (2R)-2-((2R)-2-hydroxypentyl)piperidine-1-carboxylate 
• 1421054-49-0 ((2R,4S,6R)-4-acrylamido-6-propyltetrahydro-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate 
• 1421054-50-3 N-((2R,4S,6R)-2-(iodomethyl)-6-propyltetrahydro-2H-pyran-4-yl)acrylamide 
• 1421054-51-4 N-((4R,6R)-6-hydroxynon-1-en-4-yl)acrylamide 
• 1421054-52-5 N-((4R,6R)-6-((tert-butyldimethylsilyl)oxy)non-1-en-4-yl)acrylamide 
• 1421054-53-6 (R)-6-((R)-2-((tert-butyldimethylsilyl)oxy)pentyl)-5,6-dihydropyridin-2(1H)-one 

Relevant academic research and scientific papers

Stereoselective synthesis of 2-(2-hydroxyalkyl)piperidine alkaloids through prins-ritter reaction

A stereoselective total synthesis of the 2-(2-hydroxyalkyl)piperidine alkaloids has been accomplished by a Prins-Ritter amidation sequence. Other steps involved in this synthesis are Jacobsen's hydrolytic kinetic resolution (HRK) and ring-closing metathes

Organocatalytic stereoselective approach to the total synthesis of (-)-halosaline

A practical and efficient organocatalytic approach to the synthesis of substituted piperidine alkaloids in high enantio- and diastereomeric excess was achieved using proline-catalyzed sequential α-aminoxylation/α- amination reaction and HWE olefination reaction of an aldehyde.

Stereoselective synthesis of anti-1,3-aminoalcohols via reductive opening of 4-amidotetrahydropyrans derived from the Prins/Ritter sequence

A novel method has been devised for anti-1,3-aminoalcohols through reductive elimination of iodomethyltetrahydropyrans which are in turn derived from a Prins/Ritter reaction sequence. The synthetic versatility of this method has been explored in the total

Hydroformylation of alkenylamines. Concise approaches toward piperidines, quinolizidines, and related alkaloids

Linear hydroformylation of N-protected allyl- or homoallylamines (cyclohydrocarbonylation: CHC), followed by a reductive amination constitute the two key steps toward convenient routes to aza-heterocycles.

Cyclopentanone ring expansion leading to functionalized δ-lactams: Short synthesis of simple sedum alkaloids

Equation Presented Monosubstituted epoxides react with (cyclopentenyloxy) trimethylsilane to afford, after subsequent oxidative fragmentation, a pair of diastereomeric 8-membered iodolactones. When these lactones are separately treated with sodium azide,

Concise asymmetric synthesis of (-)-halosaline and (2R,9aR)-(+)-2-hydroxy- quinolizidine by ruthenium-catalyzed ring-rearrangement metathesis

A ruthenium-catalyzed ring opening-ring closing metathesis reaction serves as the key step in the stereoselective synthesis of a new enantiopure 2-substituted-4,5-dehydropiperidine skeleton, a valuable intermediate for the synthesis of piperidine alkaloid

Development and application of a new general method for the asymmetric synthesis of syn- and anti-1,3-amino alcohols

A general method is described for asymmetric synthesis of both syn- and anti-1,3-amino alcohols. The first application of metalloenamines derived from N-sulfinyl imines is reported for the highly diastereoselective addition to aldehydes. The reduction of the product β-hydroxy N-sulfinyl imines 2 with catecholborane and LiBHEt3 provides syn- and anti-1,3-amino alcohols with very high diastereomeric ratios. This method was found to be effective for a variety of substrates incorporating either aromatic or various aliphatic substituents. The convergent and efficient asymmetric syntheses of the two natural products, (-)-8-epihalosaline and (-)-halosaline, were also accomplished.

Total synthesis of (-)-halosaline by a ruthenium-catalyzed ring rearrangement

The stereoselective synthesis of substituted piperidines by a ruthenium- catalyzed ring rearrangement of cyclopentene derivatives is demonstrated. The influence of different substituents and the effect of ethylene on the metathesis reaction is described. The ring rearrangement can be combined with a molybdenum-catalyzed cross metathesis reaction using allyltrimethyl silane as coupling partner. The first total synthesis of (-)-halosaline was accomplished via domino metathesis reaction utilizing Grubbs' ruthenium catalyst.

A new synthesis of all four stereoisomers of 2-(2,3- dihydroxypropyl)piperidine via iterative asymmetric dihydroxylation to cause enantiomeric enhancement. Application to asymmetric synthesis of naturally occurring piperidine-related alkaloids

Both enantiomers of 2-(2-propenyl)piperidine 1 (76-88% ee), prepared via the first asymmetric dihydroxylation (AD) of 5-hexenyl azide, underwent the second AD to provide all four of the stereoisomeric 2-(2,3- dihydroxypropyl)piperidines 2 with enantiomeric enhancement.(>98% ee). An asymmetric synthesis, starting from 2, of several 2-(2- hydroxyalkyl)piperidine alkaloids [(-)halosaline, (+)-N-methylallosedridine, (+)-8-ethylnorlobelol, (+)-sedridine, (+)-allosedridine, (-)allosedridine, and (+)-N-methylsedridine] and the ant defense alkaloids [(+)-tetraponerine-3 (T-3), T-4, T-7, and T-8] is demonstrated.

A general entry to 2-(2-hydroxyalkyl)piperidines via iterative asymmetric dihydroxylation to cause enantiomeric enhancement

Both enantiomers of 2-(2-propenyl)piperidine (1) (76-88% ee), prepared via the first AD of 5-hexenyl azide, underwent the second AD to provide all of the four stereoisomeric 2-(2-hydroxypropyl)piperidines (2) with enantiomeric enhancement (>98 ee). An asy