109668-52-2

Upstream product

• 194346-28-6 [(4R,5R)-5-((E)-3-Hydroxy-2-methyl-propenyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-carbamic acid methyl ester 
• 122866-07-3 <2aα,4β,5α(E)>-(+/-)-3-(1-acetyl-1,2,2a,3,4,5-hexahydro-4-(methylamino)benzindol-5-yl)-2-methylprop-2-enyl acetate 
• 122866-07-3 <2aα,4β,5α(Z)>-(+/-)-3-(1-acetyl-1,2,2a,3,4,5-hexahydro-4-(methylamino)benzindol-5-yl)-2-methylprop-2-enyl acetate 
• 106507-95-3 [(4S,5S)-5-((Z)-3-Hydroxy-2-methyl-propenyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-carbamic acid methyl ester 
• 1074-86-8 4-formyl indole 
• 76084-20-3 (E)-methyl 3-(1H-indol-4-yl)acrylate 
• 76084-22-5 (E)-3-[3-(2-Oxo-ethyl)-1H-indol-4-yl]-acrylic acid methyl ester 
• 76084-21-4 (E)-methyl-3-(3-cyanomethyl-4-indolyl)propenoate 
• 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 
• 76084-14-5 methyl(6aR^*,9S^*,9aS^*)-4,6,6a,7,9,9a-hexahydro-7-methylindolo<4,3 - e,f><2,1>benzisoxazole-9-carboxylate 
• 76084-17-8 t-butyl-N-<(4R^*,5S^*,1'S^*)-5-(1',2'-dihydroxyethyl)-1,3,4,5-tetrahydrobenzindol-4-yl>N-methylcarbamate 
• 76084-16-7 methyl(Z)-(4R^*,5R^*)-3-<4-(t-butoxycarbonyl)methylamino-1,3,4,5-tetrahydrobenzindol-5-yl>-2-methylpropenoate 
• 79133-62-3 (+)-4,5-cis-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole 
• 79133-62-3 4,5-trans-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenz-indole 

Downstream Products

• 548-42-5 (+/-)-Agroclavine 
• 95586-10-0 (+/-)-Agroclavine I 
• 77784-57-7 Acetic acid (E)-3-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl]-2-methyl-allyl ester 
• 77784-56-6 Acetic acid 2-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-ylmethyl]-allyl ester 

Relevant academic research and scientific papers

178. Stereoselective Total Syntheses of (+/-)-Chanoclavine I and (+/-)-Isochanoclavine I by an Intramolecular Nitrone-Olefin/Cycloaddition

The racemic alkaloids chanoclavine I (1) and isochanoclavine I (2) have been synthesized stereoselectively from indole-4-carbaldehyde (3) by a sequence of 11 operations in overall yields of 14percent and 2.4percent, respectively.The key step 6->8 (Scheme 2) involves a transient nitrone 7 which undergoes a regio- and stereoselective intramolecular cycloaddition to a 1,2-disubstituted olefinic bond.

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 synthesis of optically active chanoclavine-I

The total synthesis of optically active chanoclavine-I, an ergot alkaloid, was accomplished using palladium-catalyzed intramolecular cyclization (Heck-reaction) as a key step. The conjugate ester (6) was obtained in 2 steps from optically active 4-bromotryptophan (10), and the cyclization of 6 proceeded smoothly without racemization to give the key intermediate, tricyclic tetrahydrobenz[c,d]indole derivative (7), in high yield.

Total Synthesis of (-)-Chanoclavine i and an Oxygen-Substituted Ergoline Derivative

An efficient and direct route to ergot alkaloid (-)-chanoclavine I (3) is described using the inexpensive compound (2R)-(+)-phenyloxirane (15) as a chiral pool in 13 steps with 17% overall yield. Key features of the synthesis include a palladium-catalyzed intramolecular aminoalkynylation of terminal olefin and a rhodium-catalyzed intramolecular [3 + 2] annulation. An oxygen-substituted ergoline derivative (-)-25 was also achieved by using the same strategy.

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.

Simple total syntheses of (-)-ergot alkaloids and their (+)-enantiomers by a common synthesis method utilizing optical resolution

The first and simple total syntheses of (-)-isochanoclavine-1 ((-)-1b), (-)-agroclavine ((-)-3), (-)-agroclavine-1 ((-)-4), and (-)-norchanoclavine-1 ((-)-5c) and their (+)-enantiomers are achieved from indole-3-carboxaldehyde (8) by a common synthesis method utilizing optical resolution. Absolute configuration of (-)-agroclavine-1 is determined to be 5R and 10S for the first time. Preparations of both enantiomers of chanoclavine-1 (1c) are also included.

Photocyclisation of Enamides. Part 35. New Total Syntheses of the Ergot Alkaloids (+/-)-Chanoclavine-I and (+/-)-isochanoclavine-I using a Fragmentation of 3-Amino Alcohols

A new synthetic route involving the fragmentation reaction of 3-amino alcohols for the total synthesis of 6,7-secoergoline alkaloids was developed and then successfully applied to the total syntheses of (+/-)-chanoclavine-I and (+/-)-isochanoclavine-I.

THE FIRST TOTAL SYNTHESIS OF (+/-)-CHANOCLAVINE-I ACID AND AN ALTERNATIVE TOTAL SYNTHESIS OF (+/-)-CHANOCLAVINE-I

The total synthesis of (+/-)-chanoclavine-I acid was achieved for the first time.An alternative total synthesis of (+/-)-chanoclavine-I was also reported.

A NOVEL SYNTHESIS OF (+/-)-ISOCHANOCLAVINE-I

Total synthesis of (+/-)-isochanoclavine-I (9) was achieved via the route involving fragmentation reaction of the 3-aminoalcohol 4.

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.