Fukuyama, Tohru2009-06-042009-06-041992Linton, Steven Douglas. "A stereocontrolled total synthesis of (+,-)-renieramycin A." (1992) Diss., Rice University. <a href="https://hdl.handle.net/1911/16531">https://hdl.handle.net/1911/16531</a>.https://hdl.handle.net/1911/16531A novel synthetic route via iterative condensations of piperazinedione and substituted benzaldehydes has resulted in the first total synthesis of the complex antibiotic, renieramycin A 1a. Salient features include an acyliminium ion-mediated construction of a diazabicyclo (3.3.1) nonane nucleus, which allows for stereoselective hydrogenation and benzylic oxidation. The stereochemistry of the angelate side chain was unequivocally determined by X-ray crystallographic analysis of the penultimate intermediate, 67b. (DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI)149 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 chemistryPharmaceutical chemistryThesisThesis Chem. 1992 Linton