(6α)-14,18-Epoxy-3-hydroxy-5-oxoophiobola-7,19-dien-25-al

Base Information

• Chemical Name: (6α)-14,18-Epoxy-3-hydroxy-5-oxoophiobola-7,19-dien-25-al
• CAS No.: 24034-72-8
• Molecular Formula: C₂₅H₃₆O₄
• Molecular Weight: 400.558
• Mol file: 24034-72-8.mol

Synonyms:6a-Ophiobola-7,19-dien-25-al,14,18-epoxy-3-hydroxy-5-oxo- (8CI); Ophiobola-7,19-dien-25-al,14,18-epoxy-3-hydroxy-5-oxo-, (6a)-; Epicochliobolin A

Chemical Property of (6α)-14,18-Epoxy-3-hydroxy-5-oxoophiobola-7,19-dien-25-al

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6α)-14,18-Epoxy-3-hydroxy-5-oxoophiobola-7,19-dien-25-al

There total 51 articles about (6α)-14,18-Epoxy-3-hydroxy-5-oxoophiobola-7,19-dien-25-al which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(5α,7E,18R)-14,18-epoxyophiobola-7,19-diene-3,5,25-triol → Ophiobolin A (4611-05-6,24034-72-8,90411-19-1)

Guidance literature:

(5α,7E,18R)-14,18-epoxyophiobola-7,19-diene-3,5,25-triol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

With triethylamine; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201104447

Reference yield:

2-[(2R,4S,5S,6R,7R)-7-[((1S,2S,3S)-2-tert-butyldimethylsilyloxymethyl-3-tert-butyldiphenylsilyloxy-5-oxocyclopentyl)methyl]-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl 2,2-dimethylpropanoate (1344673-78-4) → Ophiobolin A (4611-05-6,24034-72-8,90411-19-1)

Guidance literature:

Multi-step reaction with 23 steps

1.1: diethyl ether / 2.5 h / -78 - 0 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3.2: 0 °C / Inert atmosphere

4.1: pyridinium p-toluenesulfonate / ethanol / 20 °C / Inert atmosphere

5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere

6.1: diethyl ether / 0 °C / Inert atmosphere

7.1: Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere

8.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

9.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

9.2: -78 °C / Inert atmosphere

10.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / methanol; toluene / 50 °C / Inert atmosphere

11.1: diisobutylaluminium hydride / hexane / -78 °C / Inert atmosphere

12.1: pyridine; dmap / dichloromethane / 20 °C / Inert atmosphere

13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

14.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C / Inert atmosphere

15.1: sodium hydride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere

16.1: diisobutylaluminium hydride / hexane / -78 °C / Inert atmosphere

17.1: Hoveyda-Grubbs catalyst second generation; p-benzoquinone / toluene / 110 °C / Inert atmosphere

18.1: sodium hydride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere

19.1: pyridinium p-toluenesulfonate / ethanol / 20 °C / Inert atmosphere

20.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

20.2: -78 - 20 °C / Inert atmosphere

21.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

21.2: 20 °C / Inert atmosphere

22.1: naphthalene; lithium / tetrahydrofuran / -30 °C / Inert atmosphere

23.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

23.2: -78 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; Hoveyda-Grubbs catalyst second generation; oxalyl dichloride; naphthalene; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; lithium; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; p-benzoquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Wittig reaction / 3.2: Wittig reaction / 20.1: Swern oxidation / 20.2: Swern oxidation / 21.1: Wittig reaction / 21.2: Wittig reaction / 23.1: Swern oxidation / 23.2: Swern oxidation;

DOI:10.1002/anie.201104447

Reference yield:

(1R,2S,3S,4S)-3-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxy-2-{[(2R,4S,5S,6R,7R)-2-tert-butyldiphenylsilyloxymethyl-6-(2-hydroxyethyl)-4,7-dimethyl-1-oxaspiro[4.4]non-7-yl]methyl}-1-methylcyclopentanol (1344673-92-2) → Ophiobolin A (4611-05-6,24034-72-8,90411-19-1)

Guidance literature:

Multi-step reaction with 22 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

2.2: 0 °C / Inert atmosphere

3.1: pyridinium p-toluenesulfonate / ethanol / 20 °C / Inert atmosphere

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere

5.1: diethyl ether / 0 °C / Inert atmosphere

6.1: Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere

7.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

8.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

8.2: -78 °C / Inert atmosphere

9.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / methanol; toluene / 50 °C / Inert atmosphere

10.1: diisobutylaluminium hydride / hexane / -78 °C / Inert atmosphere

11.1: pyridine; dmap / dichloromethane / 20 °C / Inert atmosphere

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

13.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C / Inert atmosphere

14.1: sodium hydride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere

15.1: diisobutylaluminium hydride / hexane / -78 °C / Inert atmosphere

16.1: Hoveyda-Grubbs catalyst second generation; p-benzoquinone / toluene / 110 °C / Inert atmosphere

17.1: sodium hydride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere

18.1: pyridinium p-toluenesulfonate / ethanol / 20 °C / Inert atmosphere

19.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

19.2: -78 - 20 °C / Inert atmosphere

20.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

20.2: 20 °C / Inert atmosphere

21.1: naphthalene; lithium / tetrahydrofuran / -30 °C / Inert atmosphere

22.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

22.2: -78 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; Hoveyda-Grubbs catalyst second generation; oxalyl dichloride; naphthalene; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; lithium; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; p-benzoquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 1.1: Swern oxidation / 1.2: Swern oxidation / 2.1: Wittig reaction / 2.2: Wittig reaction / 19.1: Swern oxidation / 19.2: Swern oxidation / 20.1: Wittig reaction / 20.2: Wittig reaction / 22.1: Swern oxidation / 22.2: Swern oxidation;

DOI:10.1002/anie.201104447

upstream raw materials:

(-)-tert-butyl-[(2R,4S,5S,6R,7S)-7-methoxymethoxymethyl-4,7-dimethyl-6-vinyl-1-oxaspiro[4.4]non-2-ylmethoxy]diphenylsilane

2-[(2R,4S,5S,6R,7S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-7-[(methoxymethoxy)methyl]-4,7-dimethyl-1-oxaspiro[4.4]nonan-6-yl]ethan-1-ol

(2R,3S,4S)-2-bromo-3-(tert-butyldimethylsilyl)oxymethyl-4-tert-butyldiphenylsilyloxycyclopentanone

(2S,3S,4S)-2-bromo-3-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxycyclopentanone

Refernces

• 1、 Tsuna, Kazuhiro,Noguchi, Naoyoshi,Nakada, Masahisa. "Enantioselective total synthesis of (+)-ophiobolin A". . p. 5476 - 5486. Retrieved 2013/06/05.