Browsing by Author "Ajeck-Carman, Karen Lynn"
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Item Synthetic studies towards the total synthesis of the saframycins(1988) Ajeck-Carman, Karen Lynn; Fukuyama, TohruA key improvement to the original saframycin B synthesis involves efficient sequential piperazinedione condensations to yield a basic saframycin skeleton from which all congeners might be made. Approaches toward the total synthesis of saframycin A result in formation of two advanced intermediates. The first, a pentacyclic diphenol nitrile with at least four out of five stereocenters established, is synthesized via a multistep scheme which involves a Pictet-Spengler type phenolic cyclization. The second advanced intermediate is produced via a route which involves cleavage of an imidazolidine ring with concomitant introduction of cyanide. An isomer of saframycin A is synthesized using this approach.