75363-29-0

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 
• 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 
• 105274-94-0 1-methoxy-6-methoxycarbonyl-6-nor-6,7-secoagroclavine 
• 67282-55-7 1-methoxy-1H-indole-3-carbaldehyde 
• 1074-86-8 4-formyl indole 
• 16136-52-0 4-cyanoindole 
• 79133-61-2 (E)-2-methyl-4-[3-(2-nitroethyl)-1H-indol-4-yl]but-3-en-2-ol 
• 76084-17-8 t-butyl-N-<(4R^*,5S^*,1'S^*)-5-(1',2'-dihydroxyethyl)-1,3,4,5-tetrahydrobenzindol-4-yl>N-methylcarbamate 
• 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 
• 112152-12-2 4--3-buten-2-one 
• 111427-30-6 4,5-cis-5-(2-methyl-1-propen-1-yl)-4-methoxycarbonylamino-1,3,4,5-tetrahydrobenz[cd]indole 
• 89368-44-5 t-butyl (4R^*,5S^*)-N-<5-(2-methyl-1-propenyl)-1,3,4,5-tetrahydrobenzindol-4-yl>N-methylcarbamate 
• 107343-13-5 4,5-cis-5-(2-methyl-1-propen-1-yl)-4-amino-1,3,4,5-tetrahydrobenz[cd]indole 
• 79133-62-3 (+)-4,5-cis-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole 

Downstream Products

• 95586-10-0 (+/-)-Agroclavine I 
• 1150-43-2 (+/-)-isochanoclavine-II 
• 548-42-5 (+/-)-Agroclavine 
• 1150-43-2 (+/-)-isochanoclavine I 

Relevant academic research and scientific papers

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.

TOTAL SYNTHESES OF (+/-)-AGROCLAVINE-I, (+/-)-6-NOR-CHANOCLAVINE-II, AND (+/-)-CHANOCLAVINE-II

The first total syntheses of (+/-)-6-nor-chanoclavine-II and (+/-)-chanoclavine-II are achieved.Total synthesis of (+/-)-agroclavine-I is also reported.

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.

TOTAL SYNTHESIS OF ERGOT ALKALOID, (+/-)-6,7-SECOAGROCLAVINE

Ergot alkaloid, (+/-)-6,7-secoagroclavine was synthesized form 2-methyl-5-nitroisoquinolinium iodide by three routes.In the course of the study, a novel intra-molecular γ-alkylation of allyl alcohol was found.Reaction of Grignard reagents with nitroalkanes to afford N-alkyl hydroxylamines was effectively used in the present synthesis.

TOTAL SYNTHESIS OF (+/-)-6,7-SECOAGROCLAVINE

An ergot alkaloid 6,7-secoagroclavine was synthesized in racemic form from 1-methoxycarbonylpyrrole in 15 steps.