Total synthesis of mitomycins

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dc.contributor.advisorFukuyama, Tohruen_US
dc.creatorYang, Lihuen_US
dc.date.accessioned2009-06-04T00:36:45Zen_US
dc.date.available2009-06-04T00:36:45Zen_US
dc.date.issued1990en_US
dc.description.abstractThe total synthesis of mitomycins via isomitomycin A is described. Key reactions are a Michael-type coupling reaction between chalcone (94)* and 5-ethylthio-2-trimethylsiloxyfuran, followed by an azido-olefin cyclization. The first route took 30 steps from 2,6-dimethoxytoluene in a overall yield of 6%. The improved second route contains 26 steps with overall yield of 10% from the same staring material. Resolution of an synthetic intermediate resulted in both (+)- and ($-$)-isomitomycin A (15). X-ray crystallographic analysis of an intermediate with known chiral auxiliary which led to the natural ($-$)-isomitomycin A unequivocally determined the absolute stereochemistry of mitomycins. ftn*Please refer to dissertation for diagrams.en_US
dc.format.extent230 p.en_US
dc.format.mimetypeapplication/pdfen_US
dc.identifier.callnoThesis Chem. 1990 Yangen_US
dc.identifier.citationYang, Lihu. "Total synthesis of mitomycins." (1990) Diss., Rice University. <a href="https://hdl.handle.net/1911/16409">https://hdl.handle.net/1911/16409</a>.en_US
dc.identifier.digitalYangLen_US
dc.identifier.urihttps://hdl.handle.net/1911/16409en_US
dc.language.isoengen_US
dc.rightsCopyright 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.en_US
dc.subjectOrganic chemistryen_US
dc.subjectPharmaceutical chemistryen_US
dc.titleTotal synthesis of mitomycinsen_US
dc.typeThesisen_US
dc.type.materialTexten_US
thesis.degree.departmentChemistryen_US
thesis.degree.disciplineNatural Sciencesen_US
thesis.degree.grantorRice Universityen_US
thesis.degree.levelDoctoralen_US
thesis.degree.nameDoctor of Philosophyen_US
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