Journal
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
Volume 83, Issue 11, Pages 1309-1322Publisher
CHEMICAL SOC JAPAN
DOI: 10.1246/bcsj.20100168
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Funding
- Japan Society for the Promotion of Science (JSPS) [15350021]
- Grants-in-Aid for Scientific Research [15350021, 21550038] Funding Source: KAKEN
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Total syntheses of sterically locked phycocyanobilin derivatives with a 15Z-anti or a 15E-anti CD-ring component were performed toward elucidation of the stereochemistry and function of the chromophore in phytochromes. In the course of the construction of a sterically locked 15E-anti CD-ring component employing 5-tosylpyrrolin-2-one derivatives as the D-ring, the Is group was found to be rearranged under acidic conditions to give a mixture of regioisomers, both of which could be transformed into the same CD-ring precursor via detosylation with a base followed by Wittig-like coupling reaction. In addition, a sterically locked 15E-anti biliverdin derivative was also synthesized.
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