meso-Methylporphyrins and -chlorins

Two efficient synthetic routes to meso-methylporphyrins and -chlorins are described. In the first, meso-formylporphyrins and -chlorins are reduced to the corresponding meso-hydroxymethyl derivatives, and after zinc chelation and treatment with acetic anhydride in pyridine, the resulting meso-acetoxy...

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Bibliographic Details
Published in:Bioorganic chemistry 1980, Vol.9 (1), p.1-26
Main Authors: Smith, Kevin M., Bisset, Graham M.F., Bushell, Michael J.
Format: Article
Language:English
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Summary:Two efficient synthetic routes to meso-methylporphyrins and -chlorins are described. In the first, meso-formylporphyrins and -chlorins are reduced to the corresponding meso-hydroxymethyl derivatives, and after zinc chelation and treatment with acetic anhydride in pyridine, the resulting meso-acetoxymethylporphyrins are reduced to meso-methyl with sodium borohydride or by catalytic hydrogenation. The second route is more efficient in that copper(II) meso-formylporphyrins and -chlorins can be reduced directly with tetra n-butylammonium borohydride in hot 1,2-dichloroethane to give the copper(II) meso-methyl analog. Using the procedures developed herein, a formal total synthesis of the meso-pheophorbide from Chlorobium chlorophyll “660” band 6 is decribed, and certain photooxidation and electrophilic deuteration problems in the meso-methylchlorin series are clarified.
ISSN:0045-2068
1090-2120
DOI:10.1016/0045-2068(80)90030-9