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ChemicalBook CAS DataBase List (+)-Griseofulvin
126-07-8

(+)-Griseofulvin synthesis

9synthesis methods
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.
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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]

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