Influencing and improving the environmental performance of a large multi-national pharmaceutical company can be achieved with the help of electronic education tools, backed up by site champions and strong site teams. This paper describes the development of two of those education tools.

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Cross-conjugated dienone 18, a known precursor to (±)-coriolin, is prepared in 13 steps from simple lactone 4. Selective epoxidation of 18 provides (±)-hypnophilin. Key steps in the synthesis of 18 include a highly efficient SN2'-anti opening of 4 to give the necessary trans-3,5-disubstituted cyclopentene 11 and the novel Sml2-induced tandem radical cyclization of aldehyde 14.

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