Pfitzner-Moffat conditions

The synthesis of latanoprost (1) commences with the lactone 5 derived from the Corey lactone (Scheme I).11 12 The early introduction of the p-phenylbenzoyl protecting group12 in this lactone affords crystalline intermediates in the synthesis that are easy to handle and purify. In the next step, the primary alcohol functionality in the lactone 5 was oxidized using Pfitzner-Moffat conditions (DCC, DMSO and phosphoric acid) to yield the aldehyde 6. The crude aldehyde was then treated with dimethyl (2-oxo-4-phenyl)-phosphonate under Wadsworth-Emmons conditions (NaH, DME) to afford the enone 7 as a white crystalline solid in 59% yield. 

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