436-41-9

Basic information

• Product Name: costaclavin
• Synonyms: costaclavin;(10β)-6,8β-Dimethylergoline;Epicostaclavin;Ergoline, 6,8-dimethyl-, (8beta,10beta)-
• CAS NO: 436-41-9
• Molecular Formula: C16H20N2
• Molecular Weight: 240.3434
• Mol File: 436-41-9.mol
• Article Data: 7

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: costaclavin(CAS DataBase Reference)
• NIST Chemistry Reference: costaclavin(436-41-9)
• EPA Substance Registry System: costaclavin(436-41-9)

Safety Data

• Hazardous Substances Data: 436-41-9(Hazardous Substances Data)

Usage

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

• 254736-54-4 (5R,8R,10R)-1-(4-methylphenyl)sulfonyl-6,8-dimethylergoline 
• 61361-26-0 4-benzoyl-5,5a,6,8,9,10-hexahydro-7,9-dimethylindolo<4,3-fg>quinolin-8(4H)-one 
• 82617-49-0 2-bromo-1-bromomethyl-3-nitrobenzene 
• 254736-53-3 1,1-dimethylethyl (4R,5S)-[1,3,4,5-tetrahydro-5-[((2RS)-2-methyl-1-propanol)-3-yl]-1-[(4-methylphenyl)sulfonyl]benz[cd]indol-4-yl]-N-methylcarbamate 
• 254736-52-2 1,1-dimethylethyl (4R,5S)-[1,3,4,5-tetrahydro-5-(2-methyl-1-propenyl)-1-[(4-methylphenyl)sulfonyl]benz[cd]indol-4-yl]-N-methylcarbamate 
• 254736-51-1 1,1-dimethylethyl (4R,5S)-[1,3,4,5-tetrahydro-5-(2-oxopropyl)-1-[(4-methylphenyl)sulfonyl]benz[cd]indol-4-yl]-N-methylcarbamate 
• 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 
• 548-43-6 elymoclavine 
• 548-42-5 agroclavine 

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.

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.

Total synthesis of optically active costaclavine (synthetic studies of indoles and related compounds part 48.)

The first total synthesis of optically active costaclavine (18), an ergot alkaloid, was accomplished starting from methyl [4R-(Z)]-[4-[[(1,1- dimethylethoxy)carbonyl]methylamino]-3,4-dihydro-1-[(4- methylphenyl)sulfonyl]benz[cd]indol-5(1H)-ylidene]acetate