Fukuyama, Tohru2009-06-042009-06-041988Ajeck-Carman, Karen Lynn. "Synthetic studies towards the total synthesis of the saframycins." (1988) Diss., Rice University. <a href="https://hdl.handle.net/1911/16123">https://hdl.handle.net/1911/16123</a>.https://hdl.handle.net/1911/16123A 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.227 p.application/pdfengCopyright is held by the author, unless otherwise indicated. Permission to reuse, publish, or reproduce the work beyond the bounds of fair use or other exemptions to copyright law must be obtained from the copyright holder.Organic chemistryThesisThesis Chem. 1988 Ajeck