Abstract
THE suggestion of Dewar1 that ring C of colchicine is 7-membered is interesting, and the arguments which he advances in favour of this merit consideration. I cannot, however, accept his statement that "Cohen, Cook and Roe have now provided evidence that ring B must be 7-membered". The paper2 to which Dewar refers merely makes a tentative suggestion that ring B might be 7-membered. The only legitimate evidence that ring B of a degradation product of colchicine (namely, deaminocolchinol methyl ether) is 7-membered is provided by experiments described in a paper by Barton, Cook and Loudon, recently submitted for publication in the Journal of the Chemical Society (and received by the Society on February 1). Consequently, Dewar's assumption in respect of the structure of this part of the colchicine molecule is based on unwarranted speculation. Incidentally, the work of Barton, Cook and Loudon fully establishes the methoxylation pattern of deaminocolchinol methyl ether, and hence probably also the orientation of the substituents in colchicine.
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References
Dewar, M. J. S., Nature, 155, 141 (1945).
Cohen, A., Cook, J. W., and Roe, E. M. F., J. Chem. Soc., 194 (1940).
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COOK, J. Structure of Colchicine. Nature 155, 479 (1945). https://doi.org/10.1038/155479a0
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DOI: https://doi.org/10.1038/155479a0
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