478-89-7

Basic information

• Product Name: (8alpha)-6,8-dimethylergoline
• Synonyms: 6,8alpha-Dimethylergoline; Ergoline, 6,8alpha-dimethyl-; ergoline, 6,8-dimethyl-, (8alpha)-
• CAS NO: 478-89-7
• Molecular Formula: C₁₆H₂₀N₂
• Molecular Weight: 240.3434
• Mol File: 478-89-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 407.5°C at 760 mmHg
• Flash Point: 200.2°C
• Density: 1.123g/cm³
• Vapor Pressure: 7.53E-07mmHg at 25°C
• Refractive Index: 1.624
• CAS DataBase Reference: (8alpha)-6,8-dimethylergoline(CAS DataBase Reference)
• NIST Chemistry Reference: (8alpha)-6,8-dimethylergoline(478-89-7)
• EPA Substance Registry System: (8alpha)-6,8-dimethylergoline(478-89-7)

Safety Data

• Hazardous Substances Data: 478-89-7(Hazardous Substances Data)

Upstream product

• 478-91-1 Lysergen 
• 269405-65-4 4-benzoyl-7,8-dimethyl-4,5,5a,7-tetrahydro-6H-indolo[4,3-fg]quinolin-8-one 
• 114249-82-0 7,9-Dimethyl-4,5,5a,6,6a,7,8,9,10,10a-decahydro-indolo[4,3-fg]quinoline 
• 51867-06-2 1-benzoyl-1,2,2a,3-tetrahydrobenzindol-4-(5H)-one 
• 74607-02-6 1-benzoyl-4-methylamino-1,2,2a,3-tetrahydrobenzindole 
• 74607-01-5 4-benzoyl-5,5a,6,8,9,10-hexahydro-9-methylindolo<4,3-fg>quinolin-8(4H)-one 
• 61361-26-0 4-benzoyl-5,5a,6,8,9,10-hexahydro-7,9-dimethylindolo<4,3-fg>quinolin-8(4H)-one 
• 76084-14-5 methyl(6aR^*,9S^*,9aS^*)-4,6,6a,7,9,9a-hexahydro-7-methylindolo<4,3 - e,f><2,1>benzisoxazole-9-carboxylate 
• 89368-47-8 methyl 5-methyl-4,7-methano-3H-<1,3>oxacino<5,6,7 - cd>indole-11-carboxylate 
• 76084-15-6 ((6aR,9S,9aS)-7-Methyl-4,6,6a,7,9,9a-hexahydro-8-oxa-4,7-diaza-cyclopenta[e]acenaphthylen-9-yl)-methanol 
• 76084-22-5 (E)-3-[3-(2-Oxo-ethyl)-1H-indol-4-yl]-acrylic acid methyl ester 
• 74059-91-9 3-(N,N-dimethylaminomethyl)-4-indolecarbaldehyde 
• 76084-20-3 (E)-methyl 3-(1H-indol-4-yl)acrylate 
• 89368-50-3 3-cyanomethylindole-4-carbaldehyde 

Relevant articles and documents

Biomimetic Total Syntheses of Ergot Alkaloids via Decarboxylative Giese Coupling

Biomimetic total syntheses of Festuclavine and Pyroclavine were achieved by a sequential radical coupling. The key steps include intramolecular decarboxylative Giese reaction to form the central C ring and 4-nitrobenzenesulfonyl (Ns)-directed indole C4-H olefination to introduce the indole C4 component. In addition, D-ring formation was completed by decarboxylative alkenylation and intramolecular SN2 reaction.

Biomimetic Total Syntheses of Clavine Alkaloids

Biomimetic total syntheses of either enantiomers of a number of ergot alkaloids, chanoclavine I (1b), chanoclavine I aldehyde (1c), pyroclavine (1e), festuclavine (1f), pibocin A (1g), 9-deacetoxyfumigaclavine C (1h), and fumigaclavine G (1i), have been achieved from seco-agroclavine (1a). The advanced intermediate for seco-agroclavine (1a) was synthesized via a key thiourea-catalyzed intramolecular nitronate addition onto α,β-unsaturated ester.

Total Syntheses of Festuclavine, Pyroclavine, Costaclavine, epi-Costaclavine, Pibocin A, 9-Deacetoxyfumigaclavine C, Fumigaclavine G, and Dihydrosetoclavine

A new approach for the divergent total synthesis of eight ergot alkaloids is reported. The approach allows the first total syntheses of pyroclavine, pibocin A, 9-deacetoxyfumigaclavine C, and fumigaclavine G and also enables the efficient synthesis of festuclavine, costaclavine, epi-costaclavine, and dihydrosetoclavine. The main feature of the synthesis is the use of an unprecedented Pd-catalyzed intramolecular Larock indole annulation/Tsuji-Trost allylation cascade to assemble the tetracyclic core in one step.