Efficient synthesis of IPL576,092: a novel anti-asthma agent.
An enantioseletive synthesis of the novel anti-asthma agent IRL576,092 (2) is described. The synthetic route developed involves stereoselective 1,2-reduction of the enone carbonyl functionality of 6 and subsequent hydroboration as the key steps. Starting from the commercially available 5-androsten-3beta-ol-17-one 3, this approach affords IPL576,092 (2) in nine steps with overall yields of 25%, employing a limited number of chromatographic steps.
Shen
Yaping
Y
Inflazyme Pharmaceuticals Ltd., Suite 425, 5600 Parkwood Way, Richmond, British Columbia, Canada V6V 2M2. yshen@inflazyme.com
Burgoyne
David L
DL
D018927:Anti-Asthmatic Agents / Q000138:chemical synthesis*; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism; D013261:Sterols / Q000138:chemical synthesis* / Q000494:pharmacology
D018927:Anti-Asthmatic Agents; C467961:IPL576,092; D013261:Sterols