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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Studies on the total synthesis of lactonamycin: construction of model ABCD ring systems.

[structure: see text] Model studies on the synthesis of the tetracyclic ABCD ring system of lactonamycin (1) are described. The key step involved the double Michael addition reaction of alcohol 8 to propynoate esters to produce the BCD units 13 and 14 of the target 1. Alternatively, double Michael addition of alcohol 8 to di-tert-butyl acetylenedcarboxylate gave the corresponding BCD ring systems 36 and 37. Acid-mediated hydrolysis of the dihydroquinone monoketal units of 13 and 14 and 36 and 37 in the presence of air gave the corresponding quinones 7 and 39. These were converted into the tetracyclic ABCD units 6, 26a, 40, and 42 of lactonamycin (1) by either dihydroxylation or epoxidation and acid-catalyzed lactonization.[1]


  1. Studies on the total synthesis of lactonamycin: construction of model ABCD ring systems. Henderson, D.A., Collier, P.N., Pavé, G., Rzepa, P., White, A.J., Burrows, J.N., Barrett, A.G. J. Org. Chem. (2006) [Pubmed]
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