Studies of the synthesis of biomarkers. X. Synthesis of 13,17-secodiacholestanes.
13,17-Secodiacholestanes (6) were synthesized from cholesterol (1) in six steps. The key intermediates, (20R)- and (20S)-diacholest-13(17)-enes (3a and 3b), underwent ozonization and reduction to provide (20R)- and (20S)-13,17-secodiacholesta-13,17-dione (5a and 5b), respectively. On Clemmensen reduction, the diones (5a and 5b) yielded the target molecule 6. The structure of an unknown biomarker was shown to be different from the proposed 6 by gas chromatographic/mass spectrometric comparison.
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Laboratory of Applied Organic Chemistry, Lanzhou University, People's Republic of China.
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D002776:Cholestanes / Q000138:chemical synthesis* / Q000737:chemistry; D002784:Cholesterol / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D015394:Molecular Structure; D012632:Secosteroids / Q000138:chemical synthesis* / Q000737:chemistry; D013261:Sterols / Q000737:chemistry
D002776:Cholestanes; D012632:Secosteroids; D013261:Sterols; D002784:Cholesterol