45977-26-2

Upstream product

• 84026-79-9 (1S,5R)-N-((R)-1-phenylethyl)-1-methyl-9-azabicyclo(3.3.1)nonan-3-one 
• 1207459-46-8 (S(S),4S)-4-N-(p-toluenesulfinyl)-4-amino-8,8-(ethylenedioxy)-nonan-2-one 
• 1207459-55-9 1-((S)-2,3,4,5-tetrahydro-6-methylpyridin-2-yl)propan-2-one 
• 84002-75-5 (1R,5S)-N-((R)-1-phenylethyl)-1-methyl-9-azabicyclo(3.3.1)nonan-3-one 
• 21889-88-3 hept-6-en-2-one 
• 88056-92-2 (-)-2-cyano-6-phenyloxazolopiperidine 
• 141848-09-1 1-Aza-2-phenyl-4-oxa-5-methoxy-7-methyltricyclo<5.4.1^5,11.0>dodecane 
• 87168-79-4 1-Benzyl-2-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1,2,3,6-tetrahydro-pyridine 
• 6302-02-9 2-acetonylpyridine 
• 87168-72-7 9-Benzyl-1-methyl-9-aza-bicyclo[3.3.1]nonan-3-one 
• 542-05-2 acetonedicarboxylic acid 
• 505-03-3 5-oxohexanal 
• 84002-79-9 3-methyl-2,7-cyclooctadienone 
• 263241-28-7 (1S,3R,5R)-1-Methyl-9-aza-bicyclo[3.3.1]nonan-3-ol 

Relevant academic research and scientific papers

Four-Step Total Synthesis of (+)-Euphococcinine and (±)-Adaline

A four-step enantiospecific total synthesis of bicyclic homotropinone alkaloid euphococcinine and a racemic synthesis of adaline were reported. Key reactions in the synthesis are the diastereoselective addition of a Wittig phosphorene to the ketimines derived from Davis-Ellman sulfinamides, ring-closing metathesis, and intramolecular Michael reactions.

METHODS AND COMPOSITIONS FOR MODULATING SPLICING

Described herein are small molecule splicing modulator compounds that modulate splicing of mRNA, such as pre-mRNA, encoded by genes, and methods of use of the small molecule splicing modulator compounds for modulating splicing and treating diseases and conditions.

Asymmetrie synthesis of substituted homotropinones from W-Sulfinyl β-Amino ketone ketals. (-)-Euphococcinine and (-)-Adaline

Sulflnlmlne-derived N-sulflnyl βamlno ketone ketals on heating with NH4OAc:HOAc undergo a four-step intramolecular Mannich cyclization cascade reaction to give homotroplnones, such as (-)-euphococclnlne, in excellent yields as single isomers. 10.1021/ol902910w

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.

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

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.

A Tandem Synthesis of (+/-)-Euphococcinine and (+/-)-Adaline

Intramolecular hydroxylamine-alkyne cyclisation of the hydroxylamines 8 and 9 afforded six-membered cyclic nitrones which without isolation underwent a tandem intramolecular dipolar cycloaddition to produce the tricyclic isoxazolidines 6 and 7 respectively.These were converted in two steps into the ladybird defence alkaloids (+/-)-euphococcinine 4 and (+/-)-adaline 5.

Asymmetric Synthesis. 26. An Expeditious Enantioselective Synthesis of the Defense Alkaloids (-)-Euphococcinine and (-)-Adaline via the CN(R,S) Method

The unnatural enantiomer (-)-euphococcinine (2) and the natural enantiomer of (-)-adaline (3), two homotropane alkaloids, were each prepared in three steps from chiral (-)-2-cyano-6-oxazolopiperidine synthon 8 by the CN(R,S) method.The key steps of these

2-CYANO Δ3 PIPERIDEINES X1: BIOMIMETIC SYNTHESIS OF THE LADYBUG ALKALOIDS OF THE ADALINE SERIES

The ladybug alkaloids 4 and 17 of the adaline series were synthesized via intramolecular Mannich reaction of the intermediate iminium-enols 13, generated from the corresponding 2-cyano-2'-alkyl-6- (propan-2-one ethylene ketal) piperidines 11 and 12.

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.