135968-45-5

Basic information

• Product Name: (+/-)-5-epi-6,7-secoagroclavine
• CAS NO: 135968-45-5
• Molecular Weight: 240.348
• Mol File: 135968-45-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (+/-)-5-epi-6,7-secoagroclavine(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-5-epi-6,7-secoagroclavine(135968-45-5)
• EPA Substance Registry System: (+/-)-5-epi-6,7-secoagroclavine(135968-45-5)

Safety Data

• Hazardous Substances Data: 135968-45-5(Hazardous Substances Data)

Upstream product

• 79133-69-0 1-[(4S,5S)-4-(Hydroxy-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl]-2-methyl-propan-2-ol 
• 917-64-6 methyl magnesium iodide 
• 79133-62-3 4,5-trans-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenz-indole 
• 72527-73-2 4-iodo-indole-3-carboxaldehyde 
• 88-72-2 1-methyl-2-nitrobenzene 
• 79133-64-5 4,5-cis-4-(N-hydroxy-N-methyl)amino-5-(2-methyl-1-propen-1-yl)-1,3,4,5-tetrahydrobenz[cd]indole 
• 79133-64-5 4,5-trans-4-(N-hydroxy-N-methyl)amino-5-(2-methyl-1-propen-1-yl)-1,3,4,5-tetrahydrobenz[cd]indole 
• 107343-13-5 4,5-cis-5-(2-methyl-1-propen-1-yl)-4-amino-1,3,4,5-tetrahydrobenz[cd]indole 
• 111427-30-6 4,5-cis-5-(2-methyl-1-propen-1-yl)-4-methoxycarbonylamino-1,3,4,5-tetrahydrobenz[cd]indole 
• 112152-12-2 4--3-buten-2-one 
• 79133-72-5 N-Methyl-N-[(4S,5S)-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-methanesulfonamide 
• 76084-17-8 t-butyl-N-<(4R^*,5S^*,1'S^*)-5-(1',2'-dihydroxyethyl)-1,3,4,5-tetrahydrobenzindol-4-yl>N-methylcarbamate 
• 79133-74-7 N-[(4S,5S)-5-(2-Hydroxy-2-methyl-propyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-N-methyl-methanesulfonamide 
• 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 

Downstream Products

• 1150-43-2 (+/-)-isochanoclavine-II 
• 95586-10-0 (+/-)-Agroclavine I 
• 548-42-5 (+/-)-Agroclavine 
• 194346-08-2 6,8-dimethyl-8,9-didehydro-ergoline 
• 1150-43-2 (+/-)-isochanoclavine I 
• 135854-00-1 (R)-3,3,3-Trifluoro-2-methoxy-N-methyl-N-[(4S,5S)-5-(2-methyl-propenyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-2-phenyl-propionamide 

Relevant articles and documents

Synthetic studies directed toward ergot alkaloids, (±)-6,7-secoagroclavine, (±)-chanoclavine-1, (±)-chanoclavine-II, and (±)-agroclavine-I, by an efficient and common synthetic route

Novel three synthetic routes to (±)-6,7-secoagroclavine were developed from either methyl 3-(3-formylindol-4-yl)acrylate, indole-4-carbaldehyde, or 4-iodoindole-3-carbaldehyde. The total syntheses of (±)-chanoclavine-I, (±)-chanoclavine-II, and (±)-agroclavine-I were accomplished as well from the synthetic intermediates involved in the synthesis of (±)-6,7-secoagroclavine, culminating in establishing an efficient and common synthetic method for ergot alkaloids.

The chemistry of indoles. XXVII. A practical synthesis of the 1-methoxy analog of an ergot alkaloid, (±)-1-methoxy-6,7- secoagroclavine

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TOTAL SYNTHESES OF CLAVINE ALKALOIDS BY AN INTRAMOLECULAR NITRONE-OLEFIN CYCLOADDITION REACTION

The racemic ergot alkaloids chanoclavine I (1) and 6,7-secoagroclavine (4) have been synthesized stereoselectively from indole-4-carboxaldehyde (7) in overall yields of 14 and 13 percent, respectively.Further syntheses of isochanoclavine I (2), paliclavine (5) and costaclavine (6), via the same isoxazolidine 18 are described.The key step 16-->18 (Scheme 4) involves a transient nitrone 17 which undergoes a kinetically controlled, regio- and stereoselective intramolecular cycloaddition to a 1,2-disubstituted olefinic bond.