34399-44-5

Basic information

• Product Name: des-N-methyl-α-obscurine
• CAS NO: 34399-44-5
• Molecular Weight: 260.379
• Mol File: 34399-44-5.mol

Chemical Properties

• CAS DataBase Reference: des-N-methyl-α-obscurine(CAS DataBase Reference)
• NIST Chemistry Reference: des-N-methyl-α-obscurine(34399-44-5)
• EPA Substance Registry System: des-N-methyl-α-obscurine(34399-44-5)

Safety Data

• Hazardous Substances Data: 34399-44-5(Hazardous Substances Data)

Upstream product

• 10333-14-9 6-methyl-1,2,3,4-tetrahydro-2-pyridone 
• 1225450-36-1 (R)-3-(9-methyl-1,4-dioxaspiro[4.5]dec-6-en-6-yl)propan-1-amine 
• 10412-98-3 5-oxohexanenitrile 
• 101693-93-0 (5R)-5-methyl-2-(phenylthio)cyclohexan-1-one 
• 88154-77-2 (5R)-5-methyl-2-(phenylsulfinyl)cyclohexan-1-one 
• 1007093-77-7 (R)-3-(4-methyl-6-oxocyclohex-1-en-1-yl)propanenitrile 
• 1225450-43-0 (R)-3-(9-methyl-1,4-dioxaspiro[4.5]dec-6-en-6-yl)propanenitrile 
• 308358-04-5 (6R)-2,2,6-trimethyl-1-oxaspiro[2.5]octan-4-one 
• 89-82-7 pulegone 
• 13984-50-4 methyl levulinate 
• 83532-71-2 7-Methyl-2,3,4,6,7,8-hexahydroquinoline 

Relevant articles and documents

Bioinspired Diversification Approach Toward the Total Synthesis of Lycodine-Type Alkaloids

Nitrogen heterocycles (azacycles) are common structural motifs in numerous pharmaceuticals, agrochemicals, and natural products. Many powerful methods have been developed and continue to be advanced for the selective installation and modification of nitrogen heterocycles through C-H functionalization and C-C cleavage approaches, revealing new strategies for the synthesis of targets containing these structural entities. Here, we report the first total syntheses of the lycodine-type Lycopodium alkaloids casuarinine H, lycoplatyrine B, lycoplatyrine A, and lycopladine F as well as the total synthesis of 8,15-dihydrohuperzine A through bioinspired late-stage diversification of a readily accessible common precursor, N-desmethyl-β-obscurine. Key steps in the syntheses include oxidative C-C bond cleavage of a piperidine ring in the core structure of the obscurine intermediate and site-selective C-H borylation of a pyridine nucleus to enable cross-coupling reactions.

Total synthesis of (+)-complanadine a using an iridium-catalyzed pyridine C-H functionalization

The total synthesis of the Lycopodium alkaloid complanadine A, which is an unsymmetrical dimer of lycodine, was achieved by exploiting a common tetracyclic precursor. Key to the success of the synthesis was the development of a late-stage site-selective C-H functionalization of a pyridine moiety to arrive at a key boronic ester intermediate.

Synthesis of the Lycopodium Alkaloid rac-α-Obscurine by 1,3-Annulation of an Enimine

Acid catalysed 1,3-annulation of 1,2,3,4-tetrahydro-6-methyl-2-oxopyridine (1) to the enimine 3, followed by methylation, provides a new regio and stereoselective route to rac-α-obscurine (5).Reduction of rac-N-desmethyl-α-obscurine with LiAlH4 yields rac-lycodine (11) and rac-deacetylflabellidine (9).A new pathway for the biogenesis of the β-amino-imine 9 is suggested.