@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{liu_allu_reddy_hood_diers_bocian_holten_lindsey_2017, title={Synthesis and photophysical characterization of bacteriochlorins equipped with integral swallowtail substituents}, volume={41}, ISSN={["1369-9261"]}, DOI={10.1039/c7nj00499k}, abstractNote={The two pyrroline units of bacteriochlorins can now bear gem-dialkyl or diaryl groups (L), which project above and below the macrocycle plane, whereas dimethyl groups generally have been accessible previously.}, number={11}, journal={NEW JOURNAL OF CHEMISTRY}, author={Liu, Yizhou and Allu, Srinivasarao and Reddy, Muthyala Nagarjuna and Hood, Don and Diers, James R. and Bocian, David F. and Holten, Dewey and Lindsey, Jonathan S.}, year={2017}, month={Jun}, pages={4360–4376} } @article{liu_lindsey_2016, title={Northern-Southern Route to Synthetic Bacteriochlorins}, volume={81}, ISSN={["1520-6904"]}, DOI={10.1021/acs.joc.6b02334}, abstractNote={A new route to bacteriochlorins via Northern-Southern (N-S) self-condensation of a dihydrodipyrrin-acetal complements a prior Eastern-Western (E-W) route. Each bacteriochlorin was prepared in five steps from an α-halopyrrole and a 2,2-dimethylpent-4-ynoic acid. The first three steps follow Jacobi's synthesis of dihydrodipyrrins: Pd-mediated coupling to form a lactone-pyrrole, Petasis reagent treatment for methenylation, and Paal-Knorr type ring closure to form the 1,2,2-trimethyl-substituted dihydrodipyrrin. Subsequent steps entail conversion of the 1-methyl group to the 1-(dimethoxymethyl) unit and acid-catalyzed self-condensation of the resulting dihydrodipyrrin-acetal. The essential differences between the N-S and E-W routes lie in (1) the location of the gem-dimethyl group (with respect to the 1-acetal unit) at the 2- versus 3-position in the dihydrodipyrrin-acetals, respectively, (2) the method of synthesis of the dihydrodipyrrins, and consequently (3) access to diverse substituted bacteriochlorins including those with substituents at the meso-positions. Ten new bacteriochlorins bearing 0-6 total aryl, alkyl, and carboethoxy substituents at the β-pyrrole and/or meso-positions have been prepared, with yields of macrocycle formation of up to 39%. Four single-crystal X-ray structures (two intermediates, two bacteriochlorins) were determined. The bacteriochlorins exhibit characteristic bacteriochlorophyll-like absorption spectra, including a Qy band in the region 713-760 nm.}, number={23}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Liu, Yizhou and Lindsey, Jonathan S.}, year={2016}, month={Dec}, pages={11882–11897} }