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ChemicalBook CAS DataBase List ALPHA-ZEARALENOL

ALPHA-ZEARALENOL synthesis

3synthesis methods
-

Yield:71030-11-0 58% ,36455-72-8 29%

Reaction Conditions:

with sodium tetrahydroborate in methanol at 0 - 20; for 3 h;Inert atmosphere;

Steps:

Preparation of b- and a-Zearalenols
Toa solution of zearalenone (60.8 mg, 0.19 mmol) in MeOH (1 mL) at 0 °C wasslowly added NaBH4 (32.5 mg, 0.96 mmol, 4.5 equiv). The mixture wasstirred under argon from 0 °C to room temperature for 3 h. The reaction mixturewas then added 5 mL of H2O and extracted with EtOAc (4 × 5 mL). Thecombined organic layers were washed with brine, dried with anhydrous Na2SO4and concentrated in vacuo. Purification of the crude residue by columnchromatography (20% EtOAc/hexanes) gave a mixture of b- and a-zearalenols, whichwere further separated by reverse phase column chromatography using 70% MeOH/H2Oas an eluent to give b-zearalenol (2) and a-zearalenol (18).

References:

Tadpetch, Kwanruthai;Kaewmee, Benyapa;Chantakaew, Kittisak;Kantee, Kawalee;Rukachaisirikul, Vatcharin;Phongpaichit, Souwalak [Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,# 15,p. 3612 - 3616] Location in patent:supporting information

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