Steroids p. 263 - 265 (1990)
Update date:2022-08-05
Topics:
Li, Tong-Shuang
Li, Yu-Lin
Liang, Xiao-Tian
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 (II), treatment of the alcohol (II) with tosyl chloride and subsequent reduction with lithium aluminum hydride yielded the target molecule (12).
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Doi:10.1016/0031-9422(90)85387-U
(1990)Doi:10.1002/chem.201502418
(2015)Doi:10.1002/jps.2600520918
(1963)Doi:10.1016/j.molstruc.2011.06.006
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(1990)Doi:10.1002/hlca.19870700508
(1987)