15486-23-4

Usage

InChI:InChI=1/C9H15NO/c1-9-4-2-3-7(10-9)5-8(11)6-9/h7,10H,2-6H2,1H3/t7-,9+/m1/s1

Upstream product

• 84002-75-5 (1R,5S)-N-((R)-1-phenylethyl)-1-methyl-9-azabicyclo(3.3.1)nonan-3-one 
• 1151797-19-1 C₁₀H₁₃NO₂ 
• 263241-27-6 (1S,3R,5R,SR)-1-(p-tolylsulfinylmethyl)-10-oxa-9-azatricyclo[3.3.1.1^3,9]decane 
• 263241-26-5 (2S,SR)-2-allyl-N-hydroxy-2-(p-tolylsulfinylmethyl)piperidine 
• 292045-87-5 (4bR,9aS,10aS)-10a-Methyl-1,2,3,9,9a,10a-hexahydro-4bH-10-oxa-4a-aza-indeno[1,2-a]indene-4-thione 
• 263241-24-3 (SR)-2-(p-tolylsulfinylmethyl)-2,3,4,5-tetrahydropyridine N-oxide 
• 263241-23-2 2-((R)-Toluene-4-sulfinylmethyl)-piperidin-1-ol 
• 226545-90-0 (3R,8aS)-2,2,8a-Trimethyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-thione 
• 34418-91-2 2,3,4,5-tetrahydropyridine N-oxide 
• 110-89-4 piperidine 
• 292045-90-0 1-(10a-methyl-1,3,4,9,9a,10a-hexahydro-2H,4bH-10-oxa-4a-aza-indeno[1,2-a]inden-4-yl)-propan-2-one 
• 263241-28-7 (1S,3R,5R)-1-Methyl-9-aza-bicyclo[3.3.1]nonan-3-ol 
• 35242-04-7 cis,cis-2,7-cyclooctadienone 
• 292045-89-7 N-methoxy-N-methyl-2-(10a-methyl-1,3,4,9,9a,10a-hexahydro-2H,4bH-10-oxa-4a-aza-indeno[1,2-a]inden-4-yl)-acetamide 

Relevant academic research and scientific papers

Stereoselective synthesis of (+)-euphococcinine and (-)-adaline

(Chemical Equation Presented) We describe the syntheses of (+)-euphococcinine and (-)-adaline, two naturally occurring alkaloids containing a quaternary carbon bearing a nitrogen atom. Key features of the syntheses are a 3,3-sigmatropic rearrangement to give an all-carbon quaternary center, a ring-closing alkene metathesis to give an 8-membered ring, and the use of a single enantiomer of p-menthane-3-carboxaldehyde to make two natural alkaloids of opposite configuration.

An efficient, asymmetric synthesis of (+)-euphococcinine

The enantioselective synthesis of (+)-euphococcinine (1), a homotropane alkaloid, has been achieved in five steps from bicyclic lactam 5. (C) 2000 Elsevier Science Ltd.

Synthesis of homochiral β-sulfinyl nitrones and their application for enantioselective synthesis of (+)-euphococcinine

Homochiral β-sulfinyl nitrones can be prepared from secondary amines in three steps. Enantioselective synthesis of defensive alkaloid (+)- euphococcinine (9) has been accomplished by means of diastereoselective allylation of homochiral β-sulfinyl nitrone

ASYMMETRIC SYNTHESES OF THE LADYBUG ALKALOID ADALINE AND 1-METHYL-9-AZABICYCLO (3.3.1)NONAN-3-ONE

The double Michael addition of benzylamine to 3-alkyl-2,7-cyclooctadienones, followed by hydrogenolysis, affords bridgehead substituted 9-azabicyclo(3.3.1)nonan-3-ones.Use of (+)-α-methylbenzylamine in the addition leads to mixtures of diastereometric adducts in unequal amounts.Although the degree of asymmetric induction is low (10-20 percent ee), the diastereomers can be easily separated, affording pure enantiomeric forms of the ladybug alkaloid adaline 1 and the Euphorbia alkaloid 3.