Stereodivergent total synthesis of chlorofusin and its all seven chromophore diastereomers. Issue 2 (14th January 2015) - Qiu, Hai-Bo
Abstract: Chlorofusin (1 ), one of few natural antagonists against p53-MDM2 interactions, is a naturally biogenetic hybrid composed of a 27-membered nonacyclopeptide and a unique chromophore through the hydrocarbon linkage with ornithine. In this article, we describe our recent achievement, in details, of developing a convenient stereodivergent route for parallel total synthesis of chlorofusin (1 ) and its all seven chromophore diastereomers (1a –1g ) in enantiopure forms, starting from a common racemic azaphilone precursor10 . The newly developed total synthesis shows the great advantages of economy, scalability, stable intermediates, high yields, ease of HPLC-free operations and reduplication. Graphical abstract: