The Synthesis of Phenanthrene-9-Methanol Analogs as Potential Antimalarial Agents.
WESTERN MICHIGAN UNIV KALAMAZOO
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The first example of an aldol condensation involving an enamine and an aromatic aldehyde in the presence of u.v. light, equimolar amount of acetic acid and catalytic amount of hydroquinone is described. This new procedure gives significantly high yields of the monocondensation products, as compared to dicondensation products. An interesting case of the existence of geometrical isomerism in 1-p-bromobenzylidene-2-indanone is provided. Elegant separation of the cis and trans isomers and their characterization using n.m.r. spectroscopy and Nuclear Overhauser Effect is described. The synthesis of 5-acephenanthrenone a key intermediate in the preparation of acephenanthrene amino alcohols as potential antimalarials, was accomplished using 1-methylphenanthrene as the starting material. The initial approach involving mono-aldol condensation of benzaldehyde with 2-indanone followed by photochemical ring closure failed to give the expected product. Author
- Organic Chemistry