Absolute Configuration and the Structure of Chlorophyll

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IAN FLEMING

University Chemical Laboratory, University of Cambridge

THE structure of chlorophyll is known in considerable detail. The correct gross structure was put forward by Hans Fischer¹ and confirmed in a beautiful synthesis by R. B. Woodward^2,3; the relative configuration of the methyl and propionic ester groups on ring D was shown to be trans by Ficken, Johns and Linstead⁴; the stereochemistry and absolute configuration of the phytyl group was shown by Burrell, Jackman and Weedon^5,6 to be 2'-trans-7'R,11'R and the relative configuration at C₁₀ was shown very recently by Wolf, Brockmann, Biere and Inhoffen^7,8 to be that in which the methoxycarbonyl group is trans to the propionic ester side chain on C₇. (A recent review⁹ mentions the first X-ray crystallographic structure determination of a chlorophyll derivative, phyllochlorin ester. Success has come late in this field, because of disordered structures in the crystals of chlorophyll derivatives. The review gives no information about the absolute configuration.) The absolute configuration at C₇ and C₈, however, was not-known and there were therefore two diastereoisomeric structures still possible for chlorophyll. This report provides the missing information and completes the structure of chlorophyll-a (and therefore of chlorophyll-b the configuration of which has been shown¹⁰ to be the same as that of chlorophyll-a).

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