105708-56-3

Basic information

• Product Name: funebral
• Synonyms: funebral
• CAS NO: 105708-56-3
• Molecular Formula: C12H15NO4
• Molecular Weight: 237.2518
• Mol File: 105708-56-3.mol

Chemical Properties

• Boiling Point: 488.3°Cat760mmHg
• Flash Point: 249.1°C
• Appearance: /
• Density: 1.34g/cm³
• Vapor Pressure: 2.38E-10mmHg at 25°C
• Refractive Index: 1.6
• CAS DataBase Reference: funebral(CAS DataBase Reference)
• NIST Chemistry Reference: funebral(105708-56-3)
• EPA Substance Registry System: funebral(105708-56-3)

Safety Data

• Hazardous Substances Data: 105708-56-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H15NO4/c1-7-8(2)17-12(16)11(7)13-9(5-14)3-4-10(13)6-15/h3-5,7-8,11,15H,6H2,1-2H3/t7-,8-,11-/m0/s1

Upstream product

• 1591626-26-4 (3S,4S,5R)-3-[(4-methoxyphenyl)amino]-4,5-dimethyldihydrofuran-2(3H)-one 
• 409113-02-6 (2S,3S)-ethyl 2-(p-methoxyphenylamino)-3-methyl-4-oxo-pentanoate 
• 1591626-28-6 C₁₈H₂₉NO₄Si 
• 911099-44-0 (3S,4S,5R/5S)-3-amino-4,5-dimethyltetrahydro-2-furanone 
• 1377151-82-0 6-(((tert-butyldimethylsilyl)oxy)methyl)-6-hydroxy-2H-pyran-3(6H)-one 
• 71392-28-4 (3S,4S,5R)-3-amino-4,5-dimethyldihydrofuran-2(3H)-one 
• 674785-80-9 (3S,4S,5R)-3-[(tert-butoxycarbonyl)amino]-4,5-dimethyltetrahydro-2-furanone 
• 112616-72-5 2,5-bis(hydroxymethyl)furan mono tetrahydropyranyl ether 
• 90693-46-2 (3S,4S,5R)-3-amino-4,5-dimethyldihydrofuran-2(3H)-one hydrochloride 
• 112616-73-6 5-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)furan-2-carbaldehyde 
• 164912-25-8 (2S,3S)-methyl 2-(tert-butoxycarbonylamino)-3-methyl-4-oxopentanoate 
• 1341205-66-0 tert-butyl (3S,4S,Z)-5-((dimethyl(phenyl)silyl)methylene)-4-methyl-2-oxotetrahydrofuran-3-ylcarbamate 
• 1341205-61-5 (S)-1-(dimethyl(phenyl)silyl)but-2-ynyl 2-(tert-butoxycarbonylamino)acetate 
• 1341205-70-6 1-((3S,4S,5R)-4,5-Dimethyl-2-oxotetrahydrofuran-3-yl)-5-((tetrahydro-2H-pyran-2-yloxy)methyl)-1H-pyrrole-2-carbaldehyde 

Downstream Products

• 90605-98-4 (-)-funebrine 

Relevant articles and documents

A Maillard approach to 2-formylpyrroles: Synthesis of magnolamide, lobechine and funebral

A convenient synthesis of the traditional medicine constituents magnolamide, lobechine and funebral is described. Construction of the 2-formylpyrrole core of these natural products was achieved by means of a Maillard reaction, involving condensation of the sugar surrogate, dihydropyranone 9, with the requisite primary amines. This approach offers a very direct and general route to the 2-formylpyrrole ring system. The synthesis of the 2-formylpyrrole core found in the traditional medicine constituents, magnolamide, lobechine and funebral, was constructed by a Maillard reaction, involving condensation of the sugar surrogate, dihydropyranone 9, with the requisite primary amines. This approach offers a very direct and general route to the 2-formylpyrrole ring system. Copyright

A Maillard Approach to 2-Formylpyrroles: Synthesis of Magnolamide, Lobechine and Funebral

A convenient synthesis of the traditional medicine constituents magnolamide, lobechine and funebral is described. Construction of the 2-formylpyrrole core of these natural products was achieved by means of a Maillard reaction, involving condensation of the sugar surrogate, dihydropyranone 9, with the requisite primary amines. This approach offers a very direct and general route to the 2-formylpyrrole ring system. The synthesis of the 2-formylpyrrole core found in the traditional medicine constituents, magnolamide, lobechine and funebral, was constructed by a Maillard reaction, involving condensation of the sugar surrogate, dihydropyranone 9, with the requisite primary amines. This approach offers a very direct and general route to the 2-formylpyrrole ring system.

Total synthesis of (-)-funebrine via Au-catalyzed regio- and stereoselective γ-butyrolactonization of allenylsilane

The stereoselective total synthesis of (-)-funebrine from 2-butyn-1-ol was described. The crucial steps in the synthesis involved the stereoselective enolate Claisen rearrangement of the (S)-α-acyloxy-α-alkynylsilane 8, the Au-catalyzed regio- and stereoselective lactonization of the allenylsilane 7, and the Paal-Knorr pyrrole condensation using an unsymmetrical 1,4-diketone 4b.

Syntheses of (-)-Funebrine and (-)-Funebral, Using Sequential Transesterification and Intramolecular Cycloaddition of a Chiral Nitrone

The first syntheses of (-)-funebrine [(-)-1] and (-)-funebral [(-)-2] are described. The syntheses feature sequential formation of nitrone VI from methyl glyoxylate (5) with oxime 6, transesterification of nitrone VI with (E)-crotyl alcohol (4), and intramolecular cycloaddition of the resulting nitrone VII bearing crotyl ester to afford cycloadduct 7 as a major product. The adduct 7 was readily elaborated to amino lactone (-)-3, the key synthetic intermediate of (-)-1 and (-)-2.