Chemistry Letters, Vol.31, No.1, 82-83, 2002
A new and convenient method for the preparation of cyclooctanone containing bis-aldol skeleton by samarium(II) iodide-mediated intramolecular aldol cyclization of omega-oxiranyl keto octanal
A polyoxy eight-membered ring compound containing a bis- aldol skeleton, 2,6-dibenzyloxy-3-(t-butyldimethylsiloxy)-7-hydroxy-8-hydroxymethyl-5-(p -methoxybenzyloxy)-4,4-dimethylcyclooctanone 1, a key synthetic intermediate of 19-hydroxypaclitaxel, was prepared in high yield from 2,6-dibenzyloxy-5-(t-buthyldimethylsiloxy)-3-(p-methoxybenzyloxy)-4,4-di methyl-8,9-oxiranyl-7-oxononanal 6 by the samarium(II) iodide-mediated intramolecular aldol cyclization.