548-43-6

Basic information

• Product Name: elymoclavine
• Synonyms: elymoclavine;8,9-Didehydro-6-methylergoline-8-methanol;Ergoline-8-Methanol,8,9-didehydro-6-Methyl-
• CAS NO: 548-43-6
• Molecular Formula: C₁₆H₁₈N₂O
• Molecular Weight: 254.331
• EINECS: 208-948-9
• Mol File: 548-43-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 251°C (rough estimate)
• Boiling Point: 397.54°C (rough estimate)
• Flash Point: 236.8°C
• Appearance: /
• Density: 1.0398 (rough estimate)
• Vapor Pressure: 1.47E-09mmHg at 25°C
• Refractive Index: 1.6240 (estimate)
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly), Pyridine (Slightly, Sonicated)
• PKA: 14?+-.0.10(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: elymoclavine(CAS DataBase Reference)
• NIST Chemistry Reference: elymoclavine(548-43-6)
• EPA Substance Registry System: elymoclavine(548-43-6)

Safety Data

• Hazardous Substances Data: 548-43-6(Hazardous Substances Data)

Usage

Uses

Elymoclavin is an ergot alkaloid in Morning Glory cultivars.

Purification Methods

It crystallises from MeOH, CHCl3, Et2O, Me2CO or *C6H6. [Beilstein 23 III/IV 2716.]

InChI:InChI=1/C16H18N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-5,7,13,15,17,19H,6,8-9H2,1H3/t13-,15-/m1/s1

Synthetic route

(6aR,10aR)-9-(tert-Butyl-dimethyl-silanyloxymethyl)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinoline (1027016-28-9) → elymoclavine (548-43-6)

Conditions	Yield
With pyridinium p-toluenesulfonate In ethanol at 20℃; for 48h;	95%

agroclavine (548-42-5) → elymoclavine (548-43-6)

Conditions	Yield
for 168h; fermentative bioconversion by Ca-alginate immibilized cells of submerged cultures of C. fusiformis W1;	90%

L-methionine (63-68-3) + D,L-mevalonic acid (150-97-0, 690-72-2, 17817-88-8, 32451-23-3) + Trp (54-12-6) → elymoclavine (548-43-6)

Conditions	Yield
With phosphate buffer pH 7.3 In water for 48h; Claviceps sp., strain SD58, medium NL 406;

Indole-3-carboxaldehyde (487-89-8) → elymoclavine (548-43-6)

Conditions

Yield

Multi-step reaction with 13 steps 1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; copper diacetate / 4 h / 110 °C / Inert atmosphere 2: dmap / acetonitrile / 0.5 h / 40 °C 3: ammonium acetate / 2 h / 70 °C 4: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 °C 5: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C 6: triethylamine / dichloromethane / 1 h / 0 - 20 °C 7: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 8: hydrogenchloride; zinc / methanol; water / 1 h 9: potassium carbonate / dichloromethane / 20 h / 20 °C 10: triethylamine / dichloromethane / 24 h / 20 °C 11: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 12: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 13: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

(E)-methyl 3-(3-formyl-1H-indol-4-yl)acrylate (115698-38-9) → elymoclavine (548-43-6)

Conditions

Yield

Multi-step reaction with 12 steps 1: dmap / acetonitrile / 0.5 h / 40 °C 2: ammonium acetate / 2 h / 70 °C 3: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 °C 4: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C 5: triethylamine / dichloromethane / 1 h / 0 - 20 °C 6: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 7: hydrogenchloride; zinc / methanol; water / 1 h 8: potassium carbonate / dichloromethane / 20 h / 20 °C 9: triethylamine / dichloromethane / 24 h / 20 °C 10: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 11: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 12: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

(E)-tert-butyl 3-formyl-4-(3-methoxy-3-oxoprop-1-en-1-yl)-1H-indole-1-carboxylate → elymoclavine (548-43-6)

Conditions

Yield

Multi-step reaction with 11 steps 1: ammonium acetate / 2 h / 70 °C 2: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 °C 3: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C 4: triethylamine / dichloromethane / 1 h / 0 - 20 °C 5: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 6: hydrogenchloride; zinc / methanol; water / 1 h 7: potassium carbonate / dichloromethane / 20 h / 20 °C 8: triethylamine / dichloromethane / 24 h / 20 °C 9: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 10: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 11: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

C19H20N2O6 → elymoclavine (548-43-6)

Conditions

Yield

Multi-step reaction with 10 steps 1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 °C 2: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C 3: triethylamine / dichloromethane / 1 h / 0 - 20 °C 4: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 5: hydrogenchloride; zinc / methanol; water / 1 h 6: potassium carbonate / dichloromethane / 20 h / 20 °C 7: triethylamine / dichloromethane / 24 h / 20 °C 8: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 9: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 10: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

C18H22N2O5 → elymoclavine (548-43-6)

Conditions

Yield

Multi-step reaction with 8 steps 1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 2: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 3: hydrogenchloride; zinc / methanol; water / 1 h 4: potassium carbonate / dichloromethane / 20 h / 20 °C 5: triethylamine / dichloromethane / 24 h / 20 °C 6: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 7: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 8: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

C20H24N2O6 → elymoclavine (548-43-6)

Conditions

Yield

Multi-step reaction with 7 steps 1: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 2: hydrogenchloride; zinc / methanol; water / 1 h 3: potassium carbonate / dichloromethane / 20 h / 20 °C 4: triethylamine / dichloromethane / 24 h / 20 °C 5: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 6: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 7: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

C18H20N2O4 → elymoclavine (548-43-6)

Conditions

Yield

Multi-step reaction with 6 steps 1: hydrogenchloride; zinc / methanol; water / 1 h 2: potassium carbonate / dichloromethane / 20 h / 20 °C 3: triethylamine / dichloromethane / 24 h / 20 °C 4: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 5: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 6: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

C30H44N2O5Si → elymoclavine (548-43-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 3: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

C18H20N2O5 → elymoclavine (548-43-6)

Conditions

Yield

Multi-step reaction with 9 steps 1: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C 2: triethylamine / dichloromethane / 1 h / 0 - 20 °C 3: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 4: hydrogenchloride; zinc / methanol; water / 1 h 5: potassium carbonate / dichloromethane / 20 h / 20 °C 6: triethylamine / dichloromethane / 24 h / 20 °C 7: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 8: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 9: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

C18H22N2O2 → elymoclavine (548-43-6)

Conditions

Yield

Multi-step reaction with 5 steps 1: potassium carbonate / dichloromethane / 20 h / 20 °C 2: triethylamine / dichloromethane / 24 h / 20 °C 3: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 4: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 5: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

C28H42N2O3Si → elymoclavine (548-43-6)

Conditions

Yield

Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 24 h / 20 °C 2: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 3: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 4: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

elymoclavine (548-43-6) + acetic anhydride (108-24-7) → 8-acetoxymethyl-6-methyl-8,9-didehydro-ergoline (5080-45-5)

Conditions	Yield
In pyridine Ambient temperature;	90%
In pyridine Ambient temperature; Yield given;

elymoclavine (548-43-6) → 9,10-dihydrolysergol (18051-16-6)

Conditions	Yield
With methanol; nickel In 1,4-dioxane Heating;	86%

elymoclavine (548-43-6) + m-Chlorobenzoyl chloride (618-46-2) → O-3-Chlorobenzoyl-elymoclavin-hydrochlorid (85893-06-7)

Conditions	Yield
With pyridine Ambient temperature;	77%

elymoclavine (548-43-6) + 4-chloro-benzoyl chloride (122-01-0) → O-4-Chlorobenzoyl-elymoclavin-hydrochlorid (85893-07-8)

Conditions	Yield
With pyridine Ambient temperature;	69%

elymoclavine (548-43-6) + 4-methoxy-benzoyl chloride (100-07-2) → O-4-Methoxybenzoyl-elymoclavin-hydrochlorid (85893-09-0)

Conditions	Yield
With pyridine at 70℃;	63%

elymoclavine (548-43-6) + 3,4,5-Trimethoxybenzoyl chloride (4521-61-3) → O-3,4,5-Trimethoxybenzoyl-elymoclavin-hydrochlorid (85893-10-3)

Conditions	Yield
With pyridine at 100℃;	62%

elymoclavine (548-43-6) + 4-methyl-benzoyl chloride (874-60-2) → O-4-Methylbenzoyl-elymoclavin-hydrochlorid (85893-08-9)

Conditions	Yield
With pyridine at 70℃;	62%

elymoclavine (548-43-6) → N-((4aR,10bR)-2-Hydroxymethyl-4-methyl-6-oxo-3,4,4a,5,6,10b-hexahydro-benzo[f]quinolin-7-yl)-formamide (73621-60-0)

Conditions	Yield
With sodium periodate; methanesulfonic acid In methanol at 25℃; for 2.75h;	50%

elymoclavine (548-43-6) + β-D-glucose pentaacetate (604-69-3) → Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethoxy)-tetrahydro-pyran-3-yl ester (180144-99-4)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In nitromethane; dichloromethane for 3h; Ambient temperature;	46%

elymoclavine (548-43-6) + 4-nitrophenyl-β-D-galactopyranoside (3150-24-1) → elymoclavine-β-D-galactoside (145603-56-1) + GAL-β(1-6)-GAL-β-O-elymoclavine (145603-59-4)

Conditions	Yield
In various solvent(s) at 24℃; for 3h; β-galactosidase from Aspergillus orizae or from Escherichia coli; other ergot alkaloids;	A 37% B n/a
With 2-hydroxyethanethiol; citric acid; magnesium chloride at 24℃; for 3h; β-galactosidase from Aspergillus oryzae, K-Pi-buffer;	A 37% B n/a
With 2-hydroxyethanethiol; citric acid; magnesium chloride at 24℃; β-galactosidase from Aspergillus oryzae, K-Pi buffer;	A n/a B 1%

elymoclavine (548-43-6) + Sucrose (57-50-1) → (2R,3S,4S,5R)-2,5-Bis-hydroxymethyl-2-((6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethoxy)-tetrahydro-furan-3,4-diol

Conditions	Yield
With succinic acid; DL-5-fluorotryptophan In water at 24℃; for 1296h; Claviceps purpurea 88-EP-47;	24%

elymoclavine (548-43-6) + 4-nitrophenyl α-D-galactoside (7493-95-0) → (2R,3R,4S,5R,6R)-2-[(2R,3S,4S,5R,6S)-3,5-Dihydroxy-2-hydroxymethyl-6-((6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethoxy)-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol + (2R,3R,4S,5R,6S)-2-Hydroxymethyl-6-((6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethoxy)-tetrahydro-pyran-3,4,5-triol

Conditions	Yield
With α-galactosidase form A. oryzae; citric acid at 30℃; pH 5;	A 3% B 23%

elymoclavine (548-43-6) + methyl iodide (74-88-4) → 1-Methylelymoclavin (1935-35-9)

Conditions	Yield
With potassium amide; ferric nitrate In diethyl ether; ammonia at -50 - -40℃; for 0.5h;	14%

elymoclavine (548-43-6) + 4-nitrophenyl-α-D-mannopyranoside (10357-27-4) → (2R,3S,4S,5S,6S)-2-Hydroxymethyl-6-((6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethoxy)-tetrahydro-pyran-3,4,5-triol

Conditions	Yield
With α-mannosidase (almond); citric acid at 30℃; pH 5;	3%

elymoclavine (548-43-6) → Lysergen (478-91-1)

Conditions	Yield
With sodium; butan-1-ol

elymoclavine (548-43-6) → agroclavine (548-42-5)

Conditions	Yield
With sodium; butan-1-ol

elymoclavine (548-43-6) → (+)-Costaclavine (436-41-9, 478-89-7, 569-26-6, 40759-95-3, 61425-10-3, 74644-94-3, 74644-95-4, 74644-96-5)

Conditions	Yield
With sodium; butan-1-ol
Multi-step reaction with 2 steps 1: sodium; butan-1-ol 2: sodium; butan-1-ol View Scheme

elymoclavine (548-43-6) + tert-butyldimethylsilyl chloride (18162-48-6) → (6aR,10aR)-9-(tert-Butyl-dimethyl-silanyloxymethyl)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinoline (1027016-28-9)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 1h; Ambient temperature;

elymoclavine (548-43-6) → 8-chloromethyl-6-methyl-8,9-didehydro-ergoline (56862-50-1)

Conditions	Yield
With trichlorophosphate for 1.5h; Heating;
With oxalyl dichloride In N,N-dimethyl-formamide; acetonitrile at -70℃;

elymoclavine (548-43-6) → ((6aR,7R,10aR)-7-Methyl-7-oxy-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-yl)-methanol + ((6aR,7S,10aR)-7-Methyl-7-oxy-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-yl)-methanol

Conditions	Yield
With dihydrogen peroxide In isopropyl alcohol at 60℃; for 2h; Yield given. Yields of byproduct given;

Cyclopentanecarboxylic acid chloride (4524-93-0) + elymoclavine (548-43-6) → Cyclopentanecarboxylic acid (6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethyl ester

Conditions	Yield
With pyridine; dmap for 12h; Ambient temperature;

toluene-4-sulfonic acid isopropyl ester (2307-69-9) + elymoclavine (548-43-6) → 1-isopropylelymoclavine

Conditions	Yield
With potassium hydroxide; 18-crown-6 ether In dimethyl sulfoxide for 1h;

cycloheptanecarbonyl chloride (6557-86-4) + elymoclavine (548-43-6) → Cycloheptanecarboxylic acid (6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethyl ester

Conditions	Yield
With pyridine; dmap for 12h; Ambient temperature;

elymoclavine (548-43-6) + cyclohexanylcarbonyl chloride (2719-27-9) → Cyclohexanecarboxylic acid (6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethyl ester

Conditions	Yield
With pyridine; dmap for 12h; Ambient temperature;

elymoclavine (548-43-6) + 4-methoxy-cyclohexanecarbonyl chloride → 4-Methoxy-cyclohexanecarboxylic acid (6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethyl ester

Conditions	Yield
With pyridine; dmap for 12h; Ambient temperature;

elymoclavine (548-43-6) + Cyclobutanecarbonyl chloride (5006-22-4) → Cyclobutanecarboxylic acid (6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethyl ester

Conditions	Yield
With pyridine; dmap for 12h; Ambient temperature;

Upstream product

• 84936-67-4 (3aβ,5aβ,6aβ,11bα,11cβ)-8-benzoyl-5,5a,6,6a,7,8,11b,11c-octahydro-5-methylfuro<3,2-c>indolo<4,3-fg>quinolin-4(3aH)-one 
• 91106-44-4 (3β,8α,9α)-1-Benzyl-2,3-dihydro-8-hydroxymethyl-6-methylergolin-9-ol 
• 91106-45-5 (3β,8α,9α)-2,3-Dihydro-8-hydroxymethyl-6-methylergolin-9-ol 
• 91106-46-6 (3β,8α,9α)-1-Acetyl-8-acetoxymethyl-2,3-dihydro-6-methylergolin-9-ol 
• 91106-35-3 (3β)-1-Acetyl-8-acetoxymethyl-2,3-dihydro-8,9-didehydro-6-methylergoline 
• 91106-36-4 (3β)-2,3-Dihydroelymoclavine 
• 1027016-28-9 (6aR,10aR)-9-(tert-Butyl-dimethyl-silanyloxymethyl)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinoline 
• 115698-38-9 (E)-methyl 3-(3-formyl-1H-indol-4-yl)acrylate 
• 487-89-8 Indole-3-carboxaldehyde 
• 63-68-3 L-methionine 
• 150-97-0 D,L-mevalonic acid 
• 54-12-6 Trp 
• 548-42-5 agroclavine 

Downstream Products

• 548-42-5 agroclavine 
• 436-41-9 (+)-Costaclavine 
• 85893-06-7 O-3-Chlorobenzoyl-elymoclavin-hydrochlorid 
• 85893-07-8 O-4-Chlorobenzoyl-elymoclavin-hydrochlorid 
• 18051-16-6 9,10-dihydrolysergol 
• 478-93-3 ((6aR,9S)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl)methanol 
• 602-85-7 lysergol 
• 478-89-7 Pyroclavin 
• 189143-77-9 C₄₄H₄₀N₂O₉ 

Relevant articles and documents

Contribution to chemistry of the 6-methyl-8-ergolene-8-carbonic acid

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Dehydrogenation with Benzeneseleninic Anhydride in the Total Synthesis of Ergot Alkaloids

Investigation of the dehydrogenative conversion of indolines into indoles with benzeneseleninic anhydride (1) resulted in the development of an efficient standardised procedure, which was successfully applied to the final steps in first total synthesis of (+/-)-lysergol (18), (+/-)-isolysergol (27), and (+/-)-elymoclavine (29).

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