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Synthesis of Chlorophyll a Labeled at C(32) from Pheophorbide a Methyl Ester

✍ Scribed by Rolf Fischer; Norbert Engel; Arthur Henseler; Albert Gossauer

Book ID
102254361
Publisher
John Wiley and Sons
Year
1994
Tongue
German
Weight
377 KB
Volume
77
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

[3^2^‐^14^C]Chlorophyll a (10b) was synthesized from pheophorbide a methyl ester (5a) in a seven‐step partial synthesis. The key intermediate pheophorbide d methyl ester (6) was obtained by ozonolysis of the vinyl group of 5a in 91% yield. Selective reduction of the CHO group of 6 gave the corresponding alcohol 7, and conversion of the latter to the phosphonium bromide 8 yielded after Wittig reaction with [^14^C]paraformaldehyde, [3^2^‐^14^C]pheophorbide a methyl ester (5b). The final transformation to the title compound was achieved by acid hydrolysis of 5b, esterification with natural phytol to [3^2^‐^14^C]pheophytin a (9b), and eventual insertion of a Mg^2+^ ion.

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