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Extra info for Advanced Problems in Organic Reaction Mechanisms
CO2R RO2C / "N" ~ "O O 1, R = H 2,R-Me 42. How Mitomycin C Can Crosslink DNA Mitomycin C, 1, is a potent antitumor antibiotic discovered by Japanese scientists in fermentation cultures of Streptomyces caespitosus. It has been described as "small, fast and deadly (but very selective)" and has an extraordinary ability to crosslink the complementary strands of the DNA double helix with high efficiency and absolute specificity. It is so lethal that one crosslink per genome is sufficient to cause death of a bacterial cell.
Treatment of 3 with excess sodium hydroxide solution gave a good yield of 2. Give mechanistic explanations for (a) the presumed pathway for conversion of 1 into 2, and (b) the unusual 1,3-cyclopentanedione ~ 1,4-cyclohexanedione transformation 1 ~ 3. O R Me O O Me Me 0 1 2 3 0 Advanced Problems in Organic Reaction Mechanisms 31 Conversion of o-Hydroxyaryl Ketones into 1,2-Diacylbenzenes 56. g. 1 ~ 2. The mechanism of this very unusual replacement of a phenolic OH group by an acyl group has been studied in detail, and standard crossover experiments using, for example, a mixture of 1 and its 3,5-dibromo derivative established that the process was intramolecular.
Intramolecular Schmidt Reaction In a one-pot process which has been described as an intramolecular Schmidt reaction it has been shown that treatment of ketals or enol ethers of 1,5-azidoketones with Lewis or protic acids followed by sodium iodide in acetone results in formation of lactams in 68-95% yield. Give a mechanism for this reaction, a representative example of which is shown. O Me 1) CH 2C12/TFA N3 2) evaporate ~ 3) NaI/acetone 72% Advanced Problems in Organic Reaction Mechanisms 75. 43 lndolizidones by Intermolecular Photochemical Reaction Anthraquinone photosensitised irradiation of tertiary N-allylamines in the presence of o~13unsaturated esters gives good yields of lactams.
Advanced Problems in Organic Reaction Mechanisms by McKillop