Unlocking the Mysteries Behind the Synthesis of the “Pigments of Life”
～ Calix[3]pyrrole has finally been captured ~
- First successful synthesis of calix[3]pyrrole, an unexplored compound.
- Discovering a ring expansion reaction induced by strain.
- Unlocking a century-old mystery related to the formation of porphyrin rings, which are called the “pigments of life”.
Inokuma group devised a unique synthetic route for calix[3]pyrrole using a compound called a “carbonyl rope” and achieved the first synthesis of calix[3]pyrrole. Furthermore, the group elucidated unusual reactivity of the obtained calix[3]pyrrole under acidic conditions which are commonly used for porphyrin synthesis.
Fig. Synthesis of calix[3]pyrrole, which solved the mystery of porphyrin macrocyclization.
Original Article
Calix[3]pyrrole: A missing link in porphyrin-related chemistry
Y. Inaba, Y. Nomata, Y. Ide, J. Pirillo, Y. Hijikata, T. Yoneda, A. Osuka, J. L. Sessler, Y. Inokuma
Journal of the American Chemical Society
DOI: 10.1021/jacs.1c06331