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  • Title: Direct coupling of catharanthine and vindoline to provide vinblastine: total synthesis of (+)- and ent-(-)-vinblastine.
    Author: Ishikawa H, Colby DA, Boger DL.
    Journal: J Am Chem Soc; 2008 Jan 16; 130(2):420-1. PubMed ID: 18081297.
    Abstract:
    A direct coupling of cantharanthine with vindoline to provide vinblastine is detailed along with key mechanistic and labeling studies. Following an Fe(III)-promoted coupling reaction initiated by generation of a presumed cantharanthine amine radical cation that undergoes a subsequent oxidative fragmentation and diastereoselective coupling with vindoline, addition of the resulting reaction mixture to an Fe(III)-NaBH4/air solution leads to oxidation of the C15'-C21' double bond and reduction of the intermediate iminium ion directly providing vinblastine (43%) and leurosidine (23%), its naturally occurring C21' alcohol isomer. The yield of coupled products, which exclusively possess the natural C16' stereochemistry, approaches or exceeds 80% and the combined yield of the isomeric C21' alcohols is 66%.
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