@article{nguyen_tran_wang_zhang_wu_taniguchi_lindsey_2023, title={Four Routes to 3-(3-Methoxy-1,3-dioxopropyl)pyrrole, a Core Motif of Rings C and E in Photosynthetic Tetrapyrroles}, volume={28}, ISSN={["1420-3049"]}, url={https://doi.org/10.3390/molecules28031323}, DOI={10.3390/molecules28031323}, abstractNote={The photosynthetic tetrapyrroles share a common structural feature comprised of a β-ketoester motif embedded in an exocyclic ring (ring E). As part of a total synthesis program aimed at preparing native structures and analogues, 3-(3-methoxy-1,3-dioxopropyl)pyrrole was sought. The pyrrole is a precursor to analogues of ring C and the external framework of ring E. Four routes were developed. Routes 1–3 entail a Pd-mediated coupling process of a 3-iodopyrrole with potassium methyl malonate, whereas route 4 relies on electrophilic substitution of TIPS-pyrrole with methyl malonyl chloride. Together, the four routes afford considerable latitude. A long-term objective is to gain the capacity to create chlorophylls and bacteriochlorophylls and analogues thereof by facile de novo means for diverse studies across the photosynthetic sciences.}, number={3}, journal={MOLECULES}, author={Nguyen, Khiem Chau and Tran, Anh Thu Nguyen and Wang, Pengzhi and Zhang, Shaofei and Wu, Zhiyuan and Taniguchi, Masahiko and Lindsey, Jonathan S.}, year={2023}, month={Feb} }