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Abstract
The readily available tricyclic ester 10 has been converted to dl-camptothecin (1) in 39% yield. It was discovered that, with the C 5 carbomethoxy group in place, the C 6 benzylic position of 10 (pyridone numbering) is selectively deprotonated by sodium hexamethyldisilazide. This allows for condensation with benzaldehyde to produce acid 17 which, after ozonolysis and methylation,afforded the tricyclic keto ester 16
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