Total synthesis of mitomycins

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dc.contributor.advisorFukuyama, Tohru
dc.creatorYang, Lihu
dc.date.accessioned2009-06-04T00:36:45Z
dc.date.available2009-06-04T00:36:45Z
dc.date.issued1990
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.
dc.format.extent230 p.en_US
dc.format.mimetypeapplication/pdf
dc.identifier.callnoThesis Chem. 1990 Yang
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>.
dc.identifier.digitalYangLen_US
dc.identifier.urihttps://hdl.handle.net/1911/16409
dc.language.isoeng
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.
dc.subjectOrganic chemistry
dc.subjectPharmaceutical chemistry
dc.titleTotal synthesis of mitomycins
dc.typeThesis
dc.type.materialText
thesis.degree.departmentChemistry
thesis.degree.disciplineNatural Sciences
thesis.degree.grantorRice University
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy
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