Studies of the synthesis of biomarkers. VII. Synthesis of 5α-(17R,20R)-14,15-secocholestane (cas 131896-90-7)

Add time:07/26/2019    Source:sciencedirect.com

5α-(17R,20R)-14,15-Secocholestane (12) was synthesized from cholesterol (1) in 12 steps. The key intermediate, 5α-cholest-14-en-3β-yl acetate (4), underwent ozonization, reduction, hydrolysis, and oxidation to provide 5α-14,15-secocholesta-3,14,15-trione (8). One of the Clemmensen reduction products of 8 is 5α(17R,20R)-14,15-secocholest-15-ol (11); treatment of the alcohol (11) with tosyl chloride and subsequent reduction with lithium aluminum hydride yielded the target molecule (12).

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