ChemicalBook CAS DataBase List (+)-Griseofulvin

(+)-Griseofulvin synthesis

9synthesis methods

Product Name:(+)-Griseofulvin
CAS Number:126-07-8
Molecular formula:C17H17ClO6
Molecular Weight:352.77

Griseofulvin, 7-chloro-2,4,6-trimethoxy-6-methylspiro[benzofuran- 2(3H),1-[2]-cyclohexen]-3,4-dione (35.4.1), is an antibiotic produced by the mycelial fungus Penicillium patulum.

18113-21-8 Synthesis

18113-21-8
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126-07-8
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Yield:-

Steps:

Multi-step reaction with 12 steps
1: 93 percent / pyridine
2: 94 percent / AlCl₃ / chlorobenzene / 0.5 h / Heating
3: 73 percent / diisopropylazodicarboxylate, tributylphosphine
4: 78 percent / LHMDS / tetrahydrofuran / -78 °C
5: 95 percent / MsN₃, Et₃N
6: 62 percent / 5 mol percent of rhodium pivalate 2(piv)4> / benzene / 1 h / Heating
7: 1.) O₃, 2.) DMS / 1.) CH₂Cl₂, MeOH
8: tetrahydrofuran / Ambient temperature
9: 100 percent / TFA
10: 1.) diphenyl phosphorazidate, Et₃N, 2.) aq. HCl / 1.) toluene, reflux, 2.) reflux, 2 h
11: 49 percent / NaOMe / methanol / Ambient temperature
12: 95 percent / tetrahydrofuran / Ambient temperature

References:

Pirrung;Brown;Rege;Laughton [Journal of the American Chemical Society,1991,vol. 113,# 22,p. 8561 - 8562]

Ethanone, 1-(3-chloro-2-hydroxy-4,6-dimethoxyphenyl)-

81325-85-1
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126-07-8
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References

Phenol, 2-chloro-3,5-dimethoxy-, 1-acetate

131939-10-1
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126-07-8
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References

Ethanone, 1-[3-chloro-4,6-dimethoxy-2-[(1-methyl-2-butenyl)oxy]phenyl]-, [S-(E)]- (9CI)

136616-28-9
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126-07-8
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References

Benzenepropanoic acid, 3-chloro-4,6-dimethoxy-2-[(1-methyl-2-butenyl)oxy]-β-oxo-, methyl ester, [S-(E)]- (9CI)

136616-29-0
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126-07-8
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References

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3'-Chloropropiophenone 5-CHLORO-2-METHOXYBENZALDEHYDE Floverine 2-Hydroxy-2-methylpropiophenone 4-Chlororesorcinol Cyclohexane 2-CHLORO-3-METHOXYPHENOL 1-methoxycyclohexene 4'-hydroxy-2-methylpropiophenone 1-(3-CHLORO-4-HYDROXYPHENYL)-1-ETHANONE

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(+)-Griseofulvin synthesis

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