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dc.contributor.advisor Fukuyama, Tohru
dc.creatorYang, Lihu
dc.date.accessioned 2009-06-04T00:36:45Z
dc.date.available 2009-06-04T00:36:45Z
dc.date.issued 1990
dc.identifier.urihttps://hdl.handle.net/1911/16409
dc.description.abstract The 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.extent 230 p.
dc.format.mimetype application/pdf
dc.language.iso eng
dc.subjectOrganic chemistry
Pharmaceutical chemistry
dc.title Total synthesis of mitomycins
dc.identifier.digital YangL
dc.type.genre Thesis
dc.type.material Text
thesis.degree.department Chemistry
thesis.degree.discipline Natural Sciences
thesis.degree.grantor Rice University
thesis.degree.level Doctoral
thesis.degree.name Doctor of Philosophy
dc.identifier.citation Yang, Lihu. "Total synthesis of mitomycins." (1990) Diss., Rice University. https://hdl.handle.net/1911/16409.


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