Total Synthesis of [14C]‐Labelled Homoharringtonine

Abstract A total synthesis of enantiomerically pure [ 14 C]‐labelled (–)‐homoharringtonine in 17 steps is reported. This synthetic process enabled the production of Good Manufacturing Practice (GMP) compliant (–)‐[ 14 C]homoharringtonine that was used in a human mass balance study that was a post‐approval commitment to the U.S. Food and Drug Administration. (–)‐Homoharringtonine, also called omacetaxine mepesuccinate, is approved to treat adult patients with chronic myeloid leukemia (CML), a blood and bone marrow disease. In November 2012, the product was commercialised as Synribo ® in the U.S., marketed by Teva Pharmaceuticals.