Total Synthesis of (+)-Eburnamonine

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The enantiospecific total synthesis of vinca alkaloid (+)-eburnamonine is accomplished from <sc>l</sc>-ethyl lactate. Key feature of the synthesis is the construction of the chiral quaternary center involving a Johnson–Claisen rearrangement and assembly of the pentacyclic core by the Pictet–Spengler reaction and ring-closing metathesis.