6878-83-7

Usage

InChI:InChI=1/C11H17NO/c1-7-5-12(3)6-10-8(2)11(13)4-9(7)10/h4,7-8,10H,5-6H2,1-3H3/t7-,8-,10-/m0/s1

Upstream product

• 105406-12-0 (R)-2,4,7-Trimethyl-2,3,4,5-tetrahydro-1H-[2]pyrindine 
• 7644-13-5 1,3,4,6,7,7a-hexahydro-6-oxo-2,4,7-trimethyl-2H-2-pyrindine 
• 105406-12-0 2,4,7-trimethyl-1,2,3,4-tetrahydro-5H-2-pyrindine 
• 22324-91-0 rel(4R,7S,7aS)-2,4,7-trimethyl-1,2,3,4,7,7a-hexahydro-6H-2-pyrindin-6-ol 
• 105406-18-6 (+/-)4aβ-Hydroxy-2,4β,7β-trimethyl-1,2,3,4,4a,5,7,7a-octahydro-6H-2-pyrindine-6-one 
• 78061-70-8 (4S,7R,7aR)-6-Hydroxy-4,7-dimethyl-1,3,4,6,7,7a-hexahydro-[2]pyrindine-2-carboxylic acid ethyl ester 
• 105406-13-1 (+/-)4aβ-Hydroxy-2,4β,7-trimethyl-1,2,3,4,4a,5-hexahydro-6H-2-pyrindine-6-one 
• 78061-69-5 ethyl rel(4R,7S,7aS)-4,7-dimethyl-6-oxo-1,2,3,4,7,7a-hexahydro-6H-2-pyrindine-2-carboxylate 
• 78061-63-9 ethyl rel(3R,5S)-3-(1-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-methyl-4-oxopiperidine-1-carboxylate 
• 78061-62-8 ethyl rel(3R,4R,5S)-3-(1-(2-methyl-1,3-dioxolan-2-yl)ethyl)-4-hydroxy-5-methylpiperidine-1-carboxylate 
• 81254-64-0 ethyl 3-(1-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-methyl-1,2,3,6-tetrahydropyridine-1-carboxylate 
• 78061-65-1 ethyl rel(3R,4R,5S)-4-hydroxy-5-methyl-3-(3-oxo-2-butyl)piperidine-1-carboxylate 
• 81254-62-8 ethyl 5-methyl-3-(3-oxo-2-propyl)-1,2,3,6-tetrahydropyridine-1-carboxylate 
• 78061-57-1 ethyl 3-(3-hydroxy-2-butyl)-5-methyl-1,2,3,6-tetrahydropyridine-1-carboxylate 

Relevant academic research and scientific papers

A zirconium-mediated synthesis of (±)-tecomanine

Intramolecular cocyclisation of N-(but-2-enyl)-N-methyl-N-(2-methylbut- 3-ynyl)amine using zirconocene(ethylene), followed by carbonylation affords a 4 : 1 mixture of (±)-tecomanine and (±)-4-epi-tecomanine.

Desymmetrization of bicyclo[3.3.0]octane-3,7-dione by the Schmidt reaction: An easy synthesis of tecomanine

The C(2v) symmetry of cis-bicyclo[3.3.0]octane-3,7-dione 1 was altered by a selective Schmidt reaction to give the 3-azabicyclo[4.3.0]nonane building block 3b which was employed in a short synthesis of (±)-tecomanine 4. Asymmetric Schmidt reaction on 1, employing (2S,4R)-2-azido-4-hydroxypentane 14 as a chiral inducer, showed encouraging levels of enantiotopic methylene group stereodifferentiation.

Cyclopentenone annulation of 1,4-diketones with potassium phosphate tribasic: A synthesis of a monoterpene alkaloid, (±)-tecomanine

Conjugate addition of cyclobexanone lithium enolate to 2-nitro-2-butene and the Nef reaction on the resulting nitronate gave 2-(2-oxopropyl)cyclohexanone in good yield. Treatment of the 2-(2-oxopropyl)cyclohexanone thus obtained with potassium phosphate tribasic (K3PO4) in isopropanol gave 2,3,4,5,6,7-hexahydro-3-methyl-3aH-inden-2-one (8). Application of the procedure to 1,3-dimethyl-4-piperidone (11) gave the 1,3,4,6,7,7a-hexahydro-6-oxo-2,4,7-trimethyl-2H-2-pyrindine (12). Epimerization of 12 with basic alumina gave (±)-tecomanine (1). The short synthesis of the alkaloid demonstrates the usefulness of K3PO4 as a base for cyclopentenone annulation of 1,4-diketones without migration of the double bond.

Synthese stereospecifique de la (+/-) epi-7,7a tecomanine

The stereospecific synthesis of the (+/-) epi-7,7a tecomanine has been achieved by two stereospecific reactions starting from an amino diene N-borane.

ALCALOIDES MONOTERPENIQUES: SYNTHESE STEREOSPECIFIQUE DE LA Δ-7(7a) 4a-βH ISOTECOMANINE

The presence of an amine-borane group induces the stereoselective protonation in the γ position of the enolate 15 leading to the α,β-unsaturated ketone 4.

1,6-DIHYDRO-3(2H)-PYRIDINONES AS SYNTHETIC INTERMEDIATES. TOTAL SYNTHESIS OF (+/-)-TECOMANINE

The first and stereoselective total synthesis of (+/-)-tecomanine (1) has been achieved from ethyl 1,6-dihydro-3(2H)-pyridinone-1-carboxylate (2) as a synthon.