135626-64-1

Basic information

• Product Name: Gelsemoxonine
• Synonyms: Gelsemoxonine;14,15-Epoxy-19,20-dihydro-20-oxo-21,24-dinor-4,20-secohumantenine
• CAS NO: 135626-64-1
• Molecular Formula: C4H10O3
• Molecular Weight: 106.1204
• Mol File: 135626-64-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Gelsemoxonine(CAS DataBase Reference)
• NIST Chemistry Reference: Gelsemoxonine(135626-64-1)
• EPA Substance Registry System: Gelsemoxonine(135626-64-1)

Safety Data

• Hazardous Substances Data: 135626-64-1(Hazardous Substances Data)

Upstream product

• 1341223-32-2 benzyl ((1'S,2'S,3S,4'R,5'S,6'S)-1-methoxy-2-oxo-4'-propionyl-3',9'-dioxaspiro[indoline-3,8'-tricyclo[3.3.2.0(2,4)]decan]-6'-yl)carbamate 
• 1341221-99-5 benzyl ((1S,2S,3'S,5R)-1'-methoxy-2'-oxo-8-propionyl-6-oxaspiro[bicyclo[3.2.2]non[8]ene-4,3'-indolin]-2-yl)carbamate 
• 1341221-98-4 benzyl ((1S,2S,3'S,5R)-8-formyl-1'-methoxy-2'-oxo-6-oxaspiro[bicyclo[3.2.2]non[8]ene-4,3'-indolin]-2-yl)carbamate 
• 1341221-96-2 benzyl ((1S,2S,3'S,5S)-9-chloro-8-formyl-1'-methoxy-2'-oxo-6-oxaspiro[bicyclo[3.2.2]non[8]ene-4,3'-indolin]-2-yl)carbamate 
• 1341221-94-0 benzyl ((1S,2S,3'S,5S,E)-8-((dimethylamino)methylene)-1'-methoxy-2',9-dioxo-6-oxaspiro[bicyclo[3.2.2]nonane-4,3'-indolin]-2-yl)carbamate 
• 1341221-90-6 benzyl ((1S,2S,3'S,5S)-1'-methoxy-2',9-dioxo-6-oxaspiro[bicyclo[3.2.2]nonane-4,3'-indolin]-2-yl)carbamate 
• 1341221-88-2 (1S,2S,3'S,5S)-1'-methoxy-2',9-dioxo-6-oxaspiro[bicyclo[3.2.2]nonane-4,3'-indoline]-2-carboxylic acid 
• 1341221-86-0 (1S,2S,3'S,5S)-allyl 1'-methoxy-2',9-dioxo-6-oxaspiro[bicyclo[3.2.2]nonane-4,3'-indoline]-2-carboxylate 
• 1341221-81-5 (1S,3'S,5S)-1'-methoxy-2',9-dioxo-6-oxaspiro[bicyclo[3.2.2]non[2]ene-4,3'-indoline]-2-carbaldehyde 
• 1341222-01-2 (1S,3'S,5S)-2-(hydroxymethyl)-1'-methoxy-6-oxaspiro[bicyclo[3.2.2]non[2]ene-4,3'-indoline]-2',9-dione 
• 1341221-79-1 ((1S,3'S,5S)-1'-methoxy-2',9-dioxo-6-oxaspiro[bicyclo[3.2.2]non[2]ene-4,3'-indolin]-2-yl)methyl pivalate 
• 1397715-56-8 C₂₅H₃₃NO₆Si 
• 1341221-77-9 ((1S,6R,7R)-7-((E)-(1-methoxy-2-oxoindolin-3-ylidene)methyl)-5-oxo-3-oxabicyclo[4.1.0]heptan-7-yl)methyl pivalate 

Relevant articles and documents

Unified Total Synthesis of Five Gelsedine-Type Alkaloids: (-)-Gelsenicine, (-)-Gelsedine, (-)-Gelsedilam, (-)-14-Hydroxygelsenicine, and (-)-14,15-Dihydroxygelsenicine

The systematic arrangement of a two-carbon unit, hydrogen atom, and oxygen atom on the versatile enal moiety of a non-natural synthetic intermediate successfully led to the unified access to the gelsedine-type alkaloids. The development and use of this ne

Total synthesis of gelsemoxonine

The first total synthesis of gelsemoxonine (1) has been accomplished. Divinylcyclopropane-cycloheptadiene rearrangement of the highly functionalized substrate was successfully applied to assemble the spiro-quaternary carbon center connected to the bicyclic seven-membered core structure. A one-pot isomerization reaction of the α,β-unsaturated aldehyde to the saturated ester via the TMSCN-DBU reagent combination allowed a facile diastereoselective introduction of the latent nitrogen functionality of the unique azetidine moiety.