Total synthesis of the synthetic breast cancer drug Halaven involves stereocontrol of four centres and these were successfully derived from the聽D-quinic acid source. This allowed a crystallographic purification route in place of the chromatographic technique. It illustrates the first example of a crystallisation induced diastereoselective transformation of an 伪-methyl nitrile, as well as benefiting from the rigid bridged polycyclic system. The tangible benefits are an 80% reduction in cost and waste compared to the conventional route, largely due to the elimination of chromatography solvents, in accordance with green chemistry principles.
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