@article{oai:kanazawa-u.repo.nii.ac.jp:00010674, author = {木下, 英樹 and 藤波, 修平 and 宇梶, 裕 and 猪股, 勝彦 and Nishiyama, Kaori and Kamiya, Ayumi and Hammam, Mostafa A. S. and Kinoshita, Hideki and Fujinami, Shuhei and Ukaji, Yutaka and Inomata, Katsuhiko}, issue = {11}, journal = {Bulletin of the Chemical Society of Japan}, month = {Jan}, note = {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 Ts 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. Total syntheses of sterically locked phycocyanobilin derivatives bearing a 15Z-anti or a 15E-anti CD-ring component were performed towards elucidation of the stereochemistry and function of the chromophore in phytochromes.}, pages = {1309--1322}, title = {Total syntheses of sterically locked phycocyanobilin derivatives bearing a 15Z-anti or a 15E-anti CD-ring component}, volume = {83}, year = {2010} }