27766-71-8

Usage

InChI:InChI=1/C13H25N/c1-3-5-11-8-9-12-10(2)6-4-7-13(12)14-11/h10-14H,3-9H2,1-2H3/t10-,11+,12+,13-/m1/s1

Upstream product

• 106488-75-9 (S)-8-Methyl-3-phenyl-5-propyl-decahydro-oxazolo[2,3-j]quinoline 
• 160798-33-4 (2S,4aS,5R,8aR)-1-Benzyl-5-methyl-2-propyldecahydroquinoline 
• 22724-81-8 L-norvalinol 
• 335155-31-2 (1S,4E)-1-propylhex-4-enamine 
• 170956-17-9 (S)-1-[(4-methylphenyl)sulfonyl]-2-propylaziridin 
• 62421-38-9 4-Methyl-N-((S)-1-propyl-hex-4-ynyl)-benzenesulfonamide 
• 144375-66-6 4-Methoxy-1-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyloxycarbonyl]-3-triisopropylsilanyl-pyridinium; chloride 
• 154569-04-7 (2R,6S)-4-Oxo-2-pent-4-enyl-6-propyl-piperidine-1-carboxylic acid phenyl ester 
• 106565-71-3 (3S,5R,8aS)-3-phenylhexahydro-2H-oxazolo[3,2-a]pyridine-5-carbonitrile 
• 88794-75-6 1-Iod-4,4-dimethoxypentan 
• 154097-03-7 (4aS,5R,8aR)-5-methyl-2-propyl-3,4,4a,5,6,7,8,8a-octahydroquinoline 
• 2234-82-4 1-propylmagnesium chloride 
• 16237-19-7 1-benzyl-4,6,7,8-tetrahydro-1H,3H-quinoline-2,5-dione 
• 41609-04-5 N-benzyl-3-amino-2-cyclohexen-1-one 

Downstream Products

• 55785-30-3 (2R^*,4aS^*,5S^*,8aR^*)-2-(1-propyl)-5-methyldecahydroquinoline hydrochloride 

Relevant academic research and scientific papers

Studies on difficult intramolecular hydroaminations in the context of four syntheses of alkaloid natural products

Examples of intramolecular alkene hydroaminations forming six-membered ring systems are rare, especially for systems in which the double bond is disubstituted. Such cyclizations have important synthetic relevance. Herein we report a systematic study of these cyclizations using recently developed Cope-type hydroamination methodologies. Difficult intramolecular alkene hydroaminations were used as key steps in syntheses of 2-epi-pumiliotoxin C, coniine, N-norreticuline and desbromoarborescidine A. This effort required the development of optimized hydroamination conditions to improve the efficiency of the cyclizations. Collectively, our results show that Cope-type cyclizations can be achieved on a variety of challenging substrates and proceed under similar conditions for both N-H and N-substituted hydroxylamines.

Oxazolone cycloadducts as heterocyclic scaffolds for alkaloid construction: Synthesis of (±)-2-epi-pumiliotoxin C

Intramolecular Diels-Alder cycloaddition of N-substituted oxazolone triene I allows direct entry to the functionalized octahydroquinoline II. Further manipulation of this framework by stereo- and regioselective introduction of the 5-methyl substituent, fo

Diastereoselective synthesis of 2,5-disubstituted decahydroquinolines via ring-rearrangement metathesis and zirconium-mediated cyclization

A diastereoselective approach to 2,5-substituted decahydroquinolines by zirconium-mediated cyclization of unsaturated α,α′- disubstituted piperidines II is described. The required piperidines could be obtained from secondary sulfonamides III via ruthenium-catalyzed ring-rearrangement metathesis (RRM) in high yields. Racemic trans-195A and 2-epi-trans-195A were synthesized in 8 steps starting with butyraldehyde and cyclohex-2-enol.

The asymmetric synthesis of (-)-pumiliotoxin C using tandem catalysis

The potent neurotoxin (-)-pumiliotoxin C has been prepared in 8 steps starting from 2-cyclohexenone. Key steps are a tandem asymmetric conjugate addition-allylic substitution reaction and a tandem Heck-allylic substitution reaction. Graphical Abstract.

Efficient asymmetric synthesis of pumiliotoxin C via intramolecular [4 + 2] cycloaddition

An efficient asymmetric synthesis in nine steps of natural (-)-pumiliotoxin C (1), a decahydroquinoline alkaloid found in the skin of Central American frog species, is presented. The enantiomerically pure starting material (S)-norvalinol (3) obtained from

Enantioselective Synthesis of (-)-Pumiliotoxin C from a Chiral Amino Ester and an Acetylenic Sulfone that Acts as an Alkene Dipole Equivalent

A new synthesis of the naturally occurring (-)-enantiomer of the dendrobatid alkaloid pumiliotoxin C (1) was achieved by the conjugate addition of methyl (-)-cis-2-amino-trans-6-methylcyclohexanecarboxylate (3) to 1-(p-toluenesulfonyl)-1-pentyne (4), followed by intramolecular acylation to afford (4aS,5R,8aR)-4a,5,6,7,8,8a-hexahydro-5-methyl-2-propyl-3-(p-toluenesulfonyl)-4- quinolinone(2). The acetylenic sulfone thus acts as the synthetic equivalent of an alkene dipole species. The required enantiopure amino ester 3 was obtained by an approach based on pig liver esterase (PLE)-mediated hydrolysis. Thus, the (-)- and (+)-enantiomers of racemic dimethyl trans-3-methylcyclohexane-cis,cis-1,2-dicarboxylate (6) afforded the corresponding half-esters 7 and 8, respectively, when treated with PLE. The desired half-ester 7 was recovered intact after selective conversion of the free carboxylic acid group of the byproduct 8 into its benzyl ester. Half-ester 7 was converted into enantiopure (-)-6 with diazomethane, followed by regioselective saponification and Curtius rearrangement to afford the required enantiopure key intermediate 3. Finally, hydrogenation of the enol triflate of enaminone 2, followed by reductive desulfonylation, afforded the product (-)-1.

Use of an acetylenic sulfone as an alkene dipole equivalent in the synthesis of (±)-pumiliotoxin C

The cycloaddition of methyl cis-2-amino-trans-6-methylcyclohexanecarboxylate (3) with 1-p-(toluenesulfonyl)-1-pentyne (4) afforded the corresponding enaminone 2, that was in turn reduced to (±)-pumiliotoxin C (1). The acetylenic sulfone 4 thus functions as the synthetic equivalent of the alkene dipole 5 in this process.

Total synthesis of (-)-pumiliotoxin C by aqueous intramolecular acylnitroso Diels-Alder approach

A chiral approach to (-)-pumiliotoxin C via a stereoselective intramolecular hetero Diels-Alder reaction of a chiral acylnitroso compound performed in an aqueous medium is described.

'Decahydroquinoline construction through aza-annulation: A stereoselective synthesis of (±)-5-epipumiliotoxin C.'

Aza-annulation of activated acrylic acid derivatives with 3-benzylamino-2-cyclohexenone led to the efficient formation of the corresponding bicyclic lactam. Stereospecific hydrogenation of this unsaturated lactam resulted in the selective formation of the cis fused bicyclic alkaloid, and subsequent elaboration at C-5 and C-2 completed the synthesis of the decahydroquinoline alkaloid (±)-5-epipumiliotoxin C.

A Short, Asymmetric Synthesis of (-)-Pumiliotoxin C

An asymmetric synthesis of (-)-pumiliotoxin C is accomplished in nine steps from 4-methoxy-3-(triisopropylsilyl)pyridine.