80287-15-6

Usage

InChI:InChI=1/C17H21NO3/c1-18-9-8-17(7-6-13(19)11-16(17)18)12-4-5-14(20-2)15(10-12)21-3/h4-7,10,16H,8-9,11H2,1-3H3/t16-,17-/m0/s1

Upstream product

• 80233-05-2 4-(3,4-Dimethoxy-phenyl)-4-(2-hydroxy-ethyl)-3-methylamino-cyclohex-2-enone 
• 144692-20-6 3a-(3,4-Dimethoxy-phenyl)-1-methyl-6-oxo-2,3,3a,4,5,6-hexahydro-1H-indole-7-carboxylic acid tert-butyl ester 
• 144692-19-3 2-[3-(3,4-Dimethoxy-phenyl)-1-methyl-pyrrolidin-(2E)-ylidene]-5-methylsulfanyl-3-oxo-pentanoic acid tert-butyl ester 
• 35714-45-5 3a-(3,4-dimethoxyphenyl)-1-methyl-3,3a-dihydro-1H-indol-6(2H)-one 
• 114634-48-9 3-(3,4-Dimethoxy-phenyl)-but-3-enylamine 
• 1134201-61-8 C₁₂H₁₆O₃ 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 74-88-4 methyl iodide 
• 593-51-1 methylamine hydrochloride 
• 80233-03-0 3-(3,4-Dimethoxy-phenyl)-3-(3-oxo-butyl)-dihydro-furan-2-one 
• 80233-04-1 (S)-3a-(3,4-Dimethoxy-phenyl)-3,3a,4,5-tetrahydro-2H-benzofuran-6-one 
• 80233-02-9 3-((E)-But-2-enyl)-3-(3,4-dimethoxy-phenyl)-dihydro-furan-2-one 
• 80232-99-1 3-((E)-But-2-enyl)-3-(3,4-dimethoxy-phenyl)-5-(1-iodo-ethyl)-dihydro-furan-2-one 
• 80233-00-7 3-((E)-But-2-enyl)-3-(3,4-dimethoxy-phenyl)-5-(1-hydroxy-ethyl)-dihydro-furan-2-one 

Downstream Products

• 6023-73-0 mesembrine 

Relevant academic research and scientific papers

Functionalized Polyhydroquinolines from Amino Acids Using a Key One-Pot Cyclization Cascade and Application to the Synthesis of (±)-Δ7-Mesembrenone

Substituted polyhydroquinolines are ubiquitous skeletal cores found in drugs and bioactive natural products. As a new route to access this motif, we successfully developed a one-pot cyclization cascade with high chemocontrol and diastereoselectivity. The sequence generates two cycles, three carbon-carbon bonds, and an all-carbon quaternary center in a highly convergent process. Functionalized polyhydroquinolines and congeners can be accessed from commercially available amino acids. This versatile and robust strategy was applied to the synthesis of (±)-Δ7-mesembrenone.

Palladium-Catalyzed Allylic Alkylation via Photocatalytic Nucleophile Generation

The rapid assembly of an easily accessible terminal alkene, an aliphatic C(sp3)-H coupling partner, and allyl carbonate has been established by merging hydrogen atom transfer photocatalyst-mediated nucleophile generation and palladium-catalyzed allylic alkylation. The synthetic utility of this strategy is embodied by a concise synthesis of (±)-mesembrine. Mechanistic studies suggest that this protocol proceeds via a radical/ionic relay process, and a carbanionic species serves as a key intermediate for nucleophile attack on π-allylpalladium through a classic two-electron allylation pathway. This protocol showcases an atom-economic and environmentally friendly method to generate a nonstabilized nucleophile for transition-metal catalysis.

Pyrone Diels-Alder Routes to Indolines and Hydroindolines: Syntheses of Gracilamine, Mesembrine, and Δ7-Mesembrenone

Although the Diels-Alder reaction has long been utilized for the preparation of numerous heterocycles, opportunities to extend its power remain. Herein, we detail a simple, modular, and robust approach that combines various amines regioselectively with 4,6-dichloropyrone to create substrates which, under appropriate conditions, can directly deliver varied indolines and hydroindolines through [4+2] cycloadditions with substitution patterns difficult to access otherwise. As an initial demonstration of the power of the strategy, several different natural products have been obtained either formally or by direct total synthesis, with efforts toward one of these - the complex amaryllidaceae alkaloid gracilamine - affording the shortest route to date in terms of linear step count. Pyrone-technics: A simple, robust, and readily modifiable strategy involving [4+2]/retro-[4+2]/hydrolysis cascade sequences generates a range of indolines and hydroindolines from 4,6-dichloropyrone and appropriate amines. A 10 step synthesis was achieved of a ketone previously accessed in 15 steps, thereby accomplishing the shortest formal total synthesis of the alkaloid gracilamine. Teoc=2-(trimethylsilyl)ethoxycarbonyl.

Palladium-catalyzed sequential arylation and allylic alkylation of highly functionalized ketones: A concise synthesis of mesembrine

(Chemical Equation Presented) An unprecedented palladium-catalyzed sequential procedure toward arylation and allylic alkylation of highly functionalized cyclohexenones was developed. This new protocol leads to useful building blocks containing a benzylic

Formal syntheses of (±)-mesembrine and (±)-dihydromaritidine

Condensation of 3-arylated Δ1-pyrrolinium salts with t-butyl 3-oxopent-4-enoate 3 followed by treatment with trifluoroacetic acid yielded the alkaloid Δ7-mesembrenone 1 and its N-benzyl analogue 10. These compounds are intermediates

ANOTHER SYNTHESIS OF (+/-)-MESEMBRINE USING A SYMMETRIC STARTING MATERIAL

(+/-)-Mesembrine (10) has been synthesized efficiently via the vinylanalogous amide (9) using the symmetric substrate (1) as starting material.