Ergostan-3-ol, (3.beta.,5.alpha.,24R)- synthesis

Yield: 43% ， 57%

Reaction Conditions:

with platinum(IV) oxide;hydrogen in hexane at 20; for 0.0833333 h;Inert atmosphere;

Steps:

24R-methylcholestan-3β-ol and 24S-methylcholestan-3β-ol (6, 7)
A solution of ergosta-5,22,24 (28)-trienol (1) (5 mg, 0.01 mmol) in hexane dry (5 mL) was hydrogenated in the presence of platinum (IV) oxide (2 mg). The flask was evacuated and flushed first with argon and then with hydrogen. The reaction was stirred at room temperature under H₂ for 5 min. The catalyst was filtered through silice, and the filtrate was concentrated under vacuum. The mixture was purified by HPLC on a Nucleodur Isis 100-5 C18 (5 μm; 4.5 mm i.d. × 250 mm, Macherey-Nagel, GmbH & Co. KG, Düren, Germany) with MeOH/H₂O (999.5:0.5) as eluent (flow rate 1 mL/min) to give 1.8 mg (43% from 1) of 6 (t_R = 27 min) and 2.4 mg (57% from 1) of 7 (t_R = 28 min) as amorphous solids.

References:

Sepe, Valentina;Di Leva, Francesco Saverio;D'Amore, Claudio;Festa, Carmen;De Marino, Simona;Renga, Barbara;D'Auria, Maria Valeria;Novellino, Ettore;Limongelli, Vittorio;D'Souza, Lisette;Majik, Mahesh;Zampella, Angela;Fiorucci, Stefano [Marine Drugs,2014,vol. 12,# 6,p. 3091 - 3115]