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Issue 2, 1989
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Synthetic studies relevant to biosynthetic research on vitamin B12. Part 9. Synthesis of 20-methyl and 20-cyano isobacteriochlorins

Abstract

Isobacteriochlorins carrying a C-methyl group at C-20 of the macrocycle are important for research on the biosynthesis of vitamin B12. Several different approaches are studied which allow the introduction of a C-20 methyl group into model isobacteriochlorins, the most successful involving the stepwise reduction of a nitrile residue to a methyl group. Successful syntheses are described of two 20-methylisobacteriochlorins and two 20-cyanoisobacteriochlorins. All the routes used depend finally on the photochemical cyclisation of an 18π-electron open-chain precursor.

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Article type: Paper
DOI: 10.1039/P19890000265
Citation: J. Chem. Soc., Perkin Trans. 1, 1989,0, 265-278

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    Synthetic studies relevant to biosynthetic research on vitamin B12. Part 9. Synthesis of 20-methyl and 20-cyano isobacteriochlorins

    D. M. Arnott, P. J. Harrison, G. B. Henderson, Z. Sheng, F. J. Leeper and A. R. Battersby, J. Chem. Soc., Perkin Trans. 1, 1989, 0, 265
    DOI: 10.1039/P19890000265

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