From methyl pheophorbide-a which was used as a starting material, purpurin-7 trimethyl ester and chlorin-p6 trimethyl ester were synthesized by hydrogation-opening ring, allomerization and rearrangement reaction. The synthesis of ten unreported chlorin derivatives related to chlorophyll-a was accomplished by electrophilic adduction, electrophilic substitution, 1,3-dipolar cycloadduction and oxidation-rearrangement reaction to chemical modifications for C(3)-vinyl group, 20-meso-position, methyl group at 12-position and ester moieties at terminal positions. The structures of all new chlorins were characterized by UV, IR, 1H NMR spectra and elemental analysis.
YIN Jun-Gang
,
WANG Zhen
,
YANG Ze
,
LIU Chao
,
ZHAO Li-Li
,
WANG Jin-Jun
. Synthesis of Multi-ester Substitutied Chlorin Derivatives Related to Chlorophyll-a[J]. Chinese Journal of Organic Chemistry, 2012
, 32(02)
: 360
-367
.
DOI: 10.6023/cjoc1108301
[1] Pavlov, V. Y.; Ponomarev, G. V. Chem. Heterocycl. Compd. 2004, 40, 393.
[2] Grin, M. A.; Titeev, R. A.; Brittal, D. I.; Ulybina, O. V.; Tsiprovskiy, A. G.; Berzina, M. Y.; Lobanova, I. A.; Sivaev, I. B.; Bregadzeb, V. I.; Mironova, A. F. Mendeleev Commun. 2011, 21, 84.
[3] Wang, J.-J. Chin. J. Org. Chem. 2005, 25, 1353 (in Chinese). (王进军, 有机化学, 2005, 25, 1353.)
[4] Haas, R. N. S.; Jong, R. L. P.; Noushazare, M.; Erkelens, K.; Smijs, T. G. M.; Liu, Y.; Gast, P.; Schuitmaker, H. J.; Lugtenhurg, J. Eur. J. Org. Chem. 2004, 4024.
[5] Kozyrev, A. N.; Chen, Y.-H.; Goswami, L. N.; Tabaczynski, W. A.; Pandey, R. K. J. Org. Chem. 2006, 71, 1949.
[6] Morishita, H.; Tamiaki, H. Bioorg. Med. Chem. 2003, 11, 4049.
[7] Li, J.-J.; Liu, W.-H.; Li, F.-G.; Wang, J.-J.; Suo, Y.-R.; Liu, Y.-J. Chin. J. Org. Chem. 2007, 27, 1594 (in Chinese). (李家柱, 刘万卉, 李付国, 王进军, 索有瑞, 刘永军, 有机化学, 2007, 27, 1594.)
[8] Wang, J.-J.; Li, J.-J.; Yin, J.-G.; Liu, Y.-J. Chin. J. Org. Chem. 2008, 28, 693 (in Chinese). (王进军, 李家柱, 殷军港, 刘永军, 有机化学, 2008, 28, 693.)
[9] Wang, J.-J.; Zhang, P.; Wang, P.; Chen, G.-L.; Li, F. G. Chin. J. Org. Chem. 2010, 30, 1192 (in Chinese ). (王进军, 张朋, 王朋, 陈冠龙, 李付国, 有机化学, 2010, 30, 1192.)
[10] Wang, J.-J.; Li, F.-G.; Li, Y.-W. Chin. J. Org. Chem. 2011, 31, 68 (in Chinese). (王进军, 李付国, 李韵伟, 有机化学, 2011, 31, 68.)
[11] Smith, K. M.; Gogg, D. A.; Simpson, D. J. J. Am. Chem. Soc. 1985, 107, 4946.
[12] Wang, P. M.S. Thesis, Yantai University, Yantai, 2009 (in Chinese). (王朋, 硕士论文, 烟台大学, 烟台, 2009.)
[13] Wang, J.-J.; Li, J.-Z.; Gryko, D.; Shim, Y.-K. Bull. Korea Chem. 2006, 27, 1083.
[14] Zhang, P. M.S. Thesis, Yantai University, Yantai, 2010 (in Chinese). (张朋, 硕士论文, 烟台大学, 烟台, 2010.)
