569-26-6

Basic information

• Product Name: 6,8β-Dimethylergoline
• Synonyms: 6,8β-Dimethylergoline;Festuclavin
• CAS NO: 569-26-6
• Molecular Formula: C₁₆H₂₀N₂
• Molecular Weight: 240.3434
• Mol File: 569-26-6.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 407.5°Cat760mmHg
• Flash Point: 200.2°C
• Appearance: /
• Density: 1.123g/cm³
• Vapor Pressure: 7.53E-07mmHg at 25°C
• Refractive Index: 1.624
• CAS DataBase Reference: 6,8β-Dimethylergoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6,8β-Dimethylergoline(569-26-6)
• EPA Substance Registry System: 6,8β-Dimethylergoline(569-26-6)

Safety Data

• Hazardous Substances Data: 569-26-6(Hazardous Substances Data)

Usage

Definition

ChEBI: An alkaloid that is the 6,8beta-dimethyl derivative of ergoline.

InChI:InChI=1/C16H20N2/c1-10-6-13-12-4-3-5-14-16(12)11(8-17-14)7-15(13)18(2)9-10/h3-5,8,10,13,15,17H,6-7,9H2,1-2H3/t10-,13-,15-/m1/s1

Upstream product

• 478-91-1 Lysergen 
• 548-42-5 agroclavine 
• 548-43-6 elymoclavine 
• 254736-54-4 (5R,8R,10R)-1-(4-methylphenyl)sulfonyl-6,8-dimethylergoline 
• 186084-75-3 methyl (4R,5S)-4-[[(1,1-dimethylethoxy)carbonyl]methylamino]-1,3,4,5-tetrahydro-1-[(4-methylphenyl)sulfonyl]benz[cd]indol-5-acetate 
• 51867-27-7 6-methyl-8-piperidin-1-ylmethyl-8,9-didehydro-ergoline 
• 74059-91-9 3-(N,N-dimethylaminomethyl)-4-indolecarbaldehyde 
• 76084-22-5 (E)-3-[3-(2-Oxo-ethyl)-1H-indol-4-yl]-acrylic acid methyl ester 
• 82617-49-0 2-bromo-1-bromomethyl-3-nitrobenzene 
• 25800-42-4 (E)-2-methyl-3-((4R,5R)-4-(methylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl)acrylaldehyde 

Downstream Products

• 81967-87-5 1-methyl-festuclavine 

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.

Controlling a structural branch point in ergot alkaloid biosynthesis

The ergot alkaloids are a diverse class of fungal-derived indole alkaloid natural products with potent pharmacological activities. The biosynthetic intermediate chanoclavine-I aldehyde 1 represents a branch point in ergot biosynthesis. Ergot alkaloids festuclavine 2 and agroclavine 3 derive from alternate enzymatic pathways originating from the common biosynthetic precursor chanoclavine-I aldehyde 1. Here we show that while the Old Yellow Enzyme homologue EasA from the ergot biosynthetic gene cluster of Aspergillus fumigatus acts on chanoclavine-I aldehyde 1 to yield festuclavine 2, EasA from Neotyphodium lolii, in contrast, produces agroclavine 3. Mutational analysis suggests a mechanistic rationale for the switch in activity that controls this critical branch point of ergot alkaloid biosynthesis.