Rational Synthesis of Meso-Substituted Chlorin Building Blocks
作者:Jon-Paul Strachan、Donal F. O'Shea、Thiagarajan Balasubramanian、Jonathan S. Lindsey
DOI:10.1021/jo991942t
日期:2000.5.1
formation is achieved by a two-flask process of acid-catalyzed condensation followed by metal-mediated oxidative cyclization. The latter reaction has heretofore been performed with copper templates. Investigation of conditions for this multistep process led to copper-free conditions (zinc acetate, AgIO(3), and piperidine in toluene at 80 degrees C for 2 h). The zinc chlorin was obtained in yields of approximately
Synthesis and Electronic Properties of Regioisomerically Pure Oxochlorins
作者:Masahiko Taniguchi、Han-Je Kim、Doyoung Ra、Jennifer K. Schwartz、Christine Kirmaier、Eve Hindin、James R. Diers、Sreedharan Prathapan、David F. Bocian、Dewey Holten、Jonathan S. Lindsey
DOI:10.1021/jo025843i
日期:2002.10.1
We describe a two-step conversion of C-alkylated zinc chlorins to zinc oxochlorins wherein the keto group is located in the reduced ring (17-position) of the macrocycle. The transformation proceeds by hydroxylation upon exposure to alumina followed by dehydrogenation with DDQ. The reactions are compatible with ethyne, iodo, ester, trimethylsilyl, and pentafluorophenyl groups. A route to a spirohexyl-substituted