Selective synthesis of C3 super(2)- and C20-monoiodinated chlorophyll derivatives

A chlorophyll derivative possessing an iodine atom at the C3-moiety was synthesized from methyl pyropheophorbide-a for the first time using phenyliodine bis(trifluoroacetate) and I sub(2). The use of larger amounts of reagents resulted in additional iodination at the C20-position, thus affording the...

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Bibliographic Details
Published inTetrahedron letters Vol. 56; no. 8; pp. 999 - 1003
Main Authors Oba, Toru, Miyata, Kota, Masuya, Takuto, Yasuda, Satoru, Ito, Satoshi
Format Journal Article
LanguageEnglish
Published 18.02.2015
Subjects
Chlorophylls
Derivatives
Iodination
Iodine
Synthesis (chemistry)
Tetrahedrons
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Summary:A chlorophyll derivative possessing an iodine atom at the C3-moiety was synthesized from methyl pyropheophorbide-a for the first time using phenyliodine bis(trifluoroacetate) and I sub(2). The use of larger amounts of reagents resulted in additional iodination at the C20-position, thus affording the 3,20-diiodo derivative. The iodine atom at the C3-moiety of the 3,20-diiodo derivative could be removed selectively by treating with NaN sub(3), thus affording the 3-vinyl-20-iodo derivative.
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ISSN:0040-4039
DOI:10.1016/j.tetlet.2015.01.057