Browsing by Author "Yang, Lihu"

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    Total synthesis of mitomycins
    (1990) Yang, Lihu; Fukuyama, Tohru
    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.