@article{tran_wang_zhang_jovanovic_siewert_moser_lindsey_2024, title={Synthesis of a model phyllobilin bearing an optical marker}, volume={6}, ISSN={["1369-9261"]}, url={https://doi.org/10.1039/D4NJ01533A}, DOI={10.1039/d4nj01533a}, abstractNote={Phyllobilins – important natural products derived from chlorophylls – contain a characteristic conjugation in the southern rim, which is mimicked here in a synthetic analogue.}, journal={NEW JOURNAL OF CHEMISTRY}, author={Tran, Anh Thu Nguyen and Wang, Pengzhi and Zhang, Shaofei and Jovanovic, Milena and Siewert, Bianka and Moser, Simone and Lindsey, Jonathan S.}, year={2024}, month={Jun} }
 @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} }
 @misc{liu_zhang_lindsey_2018, title={Total synthesis campaigns toward chlorophylls and related natural hydroporphyrins - diverse macrocycles, unrealized opportunities}, volume={35}, ISSN={["1460-4752"]}, DOI={10.1039/c8np00020d}, abstractNote={Quantitative evaluation of reported routes toward bonellin, chlorophylla, and tolyporphin A suggests heuristics for practical syntheses of native hydroporphyrins.}, number={9}, journal={NATURAL PRODUCT REPORTS}, author={Liu, Yizhou and Zhang, Shaofei and Lindsey, Jonathan S.}, year={2018}, month={Sep}, pages={879–901} }
 @article{zhang_lindsey_2017, title={Construction of the Bacteriochlorin Macrocycle with Concomitant Nazarov Cyclization To Form the Annulated Isocyclic Ring: Analogues of Bacteriochlorophyll a}, volume={82}, ISSN={["0022-3263"]}, DOI={10.1021/acs.joc.6b02878}, abstractNote={Bacteriochlorophylls contain a bacteriochlorin macrocycle bearing an annulated fifth ring. The fifth ring, termed the isocyclic ring or ring E, is equipped with 131-oxo and 132-carbomethoxy substituents. Herein, a general route to stable, synthetic bacteriochlorophyll analogues is described. Knoevenagel condensation (∼40 mM, rt, CH2Cl2, piperidine/AcOH/molecular sieves) of a dihydrodipyrrin-carboxaldehyde (AD half) and a dihydrodipyrrin substituted with a β-ketoester (BC half) forms a propenone bearing the two halves (a hydrobilin analogue). Subsequent treatment (0.2 mM) with acid (Yb(OTf)3, CH3CN, 80 °C) promotes a double ring-closure process: (i) condensation between the α-position of pyrrole ring A and the α-acetal unit attached to pyrroline ring B forms the bacteriochlorin macrocycle, and (ii) Nazarov cyclization of the β-(propenoyl)-substituted ring C forms the isocyclic ring (E). Five new bacteriochlorins bearing various substituents (alkyl/alkyl, aryl, and alkyl/ester) at positions 2 and 3 (β-pyrrole sites, ring A) and 132 carboalkoxy groups (R = Me or Et) were constructed in 37-61% yield from the hydrobilin analogues. The BC half and AD half are available in five and eight steps, respectively, from the corresponding pyrrole-2-carboxaldehyde and unsaturated ketone. The bacteriochlorins exhibit absorption spectra typical of bacteriopheophytins (free base bacteriochlorophylls), with a strong near-infrared absorption band (707-751 nm).}, number={5}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Zhang, Shaofei and Lindsey, Jonathan S.}, year={2017}, month={Mar}, pages={2489–2504} }
 @article{reddy_zhang_kim_mass_taniguchi_lindsey_2017, title={Synthesis and spectral properties of meso-arylbacteriochlorins, including insights into essential motifs of their hydrodipyrrin precursors}, volume={22}, number={4}, journal={Molecules}, author={Reddy, M. N. and Zhang, S. F. and Kim, H. J. and Mass, O. and Taniguchi, M. and Lindsey, J. S.}, year={2017} }
 @article{zhang_reddy_mass_kim_hu_lindsey_2017, title={Synthesis of tailored hydrodipyrrins and their examination in directed routes to bacteriochlorins and tetradehydrocorrins}, volume={41}, DOI={10.1039/c7nj01892d}, abstractNote={18 gem-dimethyl stabilized hydrodipyrrins with diverse α-substituents have been prepared and examined in directed syntheses of unsymmetrically substituted hydroporphyrins.}, number={19}, journal={New Journal of Chemistry}, author={Zhang, S. F. and Reddy, M. N. and Mass, O. and Kim, H. J. and Hu, G. F. and Lindsey, Jonathan}, year={2017}, pages={11170–11189} }
 @article{zhang_kim_tang_yang_bocian_holten_lindsey_2016, title={Synthesis and photophysical characteristics of 2,3,12,13-tetraalkylbacteriochlorins}, volume={40}, ISSN={["1369-9261"]}, DOI={10.1039/c6nj00517a}, abstractNote={Tetraalkylbacteriochlorins, available upon acid-mediated self-condensation of α-ester stabilized dihydrodipyrrin-carboxaldehydes, provide valuable models of the naturally occurring bacteriochlorophylls.}, number={7}, journal={NEW JOURNAL OF CHEMISTRY}, author={Zhang, Shaofei and Kim, Han-Je and Tang, Qun and Yang, Eunkyung and Bocian, David F. and Holten, Dewey and Lindsey, Jonathan S.}, year={2016}, month={Jul}, pages={5942–5956} }