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Publications

Independent Research

23. Knight, B. J.; Grigolo, T. A.; Tolchin, Z. A.; Smith, J. M. "Azine Dearomatization in Natural Product Total Synthesis " Chem. Eur. J. 2025, Accepted Article.

22. Smith, J. M. "Heterocyclic Surgery for Isotopic Labeling" Synlett 2024, eFirst (invited contribution).

21. Dukes, D. M.; Atanassov, V. K.; Smith, J. M. "Enantioselective Total Synthesis of (+)-Cylindricine B" Chem. Sci. 2024, 15, 16554–16558.

20. Tolchin, Z. A.; Smith, J. M. " NRORC: An Azine Labeling Protocol" J. Am. Chem. Soc. 2024, 146, 2939–2943.

Highlighted by Chemistry Views

19. Tolchin, Z. A.; Dukes, D. M.; Gharbaoui, L. M.; Smith, J. M. "Dearomative Access to (–)-Thebaine and Derivatives " Org. Lett. 2023, 25, 8424–8428.

Highlighted by OPRD

Featured on: Synfacts

18. Knight, B. J.; Harbit, R. C.; Smith, J. M. "A Six-Step Synthesis of (±)-Lysergic Acid" J. Org. Chem. 2023, 88, 2158–2165.

To view a preprint, see: Chem Rxiv.

Featured on: Synfacts

Highlighted by Total Synthesis on YouTube

17. Piwko, A. T.; Miller, B. G.; Smith, J. M. "Revisiting the Manzamine Biosynthetic Hypothesis" Nat. Prod. Rep. 2023, 40, 964–971.

16. Grigolo, T. A.; Smith, J. M. "Regiodivergent Asymmetric Pyridinium Additions: Mechanistic Insight and Synthetic Applications" Chem. Eur. J. 2022, 28, e202202813.

Featured on: Synfacts

15. Grigolo, T. A.; Subhit, A. R.; Smith, J. M. "Regioselective Asymmetric Alkynylation of N–Alkyl Pyridiniums" Org. Lett. 2021, 23, 6703–6708.

Featured on Organic Chemistry Portal.

To view a preprint, see:ChemRxiv 2021.

14. Knight, B. J.; Tolchin, Z. A.; Smith, J. M. "A Predictive Model for Additions to N-Alkyl Pyridiniums" Chem. Commun. 2021, 57, 2693–2696.

To view a preprint see: ChemRxiv 2020.

13. Sui, X.; Grigolo, T. A.; O'Connor, C. J.; Smith, J. M. "Ortho/Ipso Alkylborylation of Aryl Iodides" Org. Lett. 2019, 21, 9251–9255.

12. Gomes, G. P.; Wimmer, A.; Smith, J. M.; König, B.; Alabugin, I. V. "CO2 or SO2 : Should It Stay or Should it Go?" J. Org. Chem. 2019, 84, 6232–6243.

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11. Smith, J. M.; Dixon, J. A.; deGruyter, J. N.; Baran, P. S. "Alkyl Sulfinates: Radical Precursors Enabling Drug Discovery" J. Med. Chem. 2019, 62, 2256–2264.

10. Smith, J. M.; Harwood, S. J.; Baran, P. S. "Radical Retrosynthesis" Acc. Chem. Res. 2018, 15, 1807–1817.

9. Picazo, E.; Morrill, L. A.; Susick, R. B.; Moreno, J.; Smith, J. M.; Garg, N. K. "Enantioselective Total Syntheses of Methanoquinolizidine-Containing Akuammiline Alkaloids and Related Studies" J. Am. Chem. Soc. 2018, 140, 6483–6492.

8. Smith, J. M.; Qin, T.; Merchant, R. R.; Edwards, J. T.; Malins, L. R.; Liu, Z.; Che, G.; Shen, Z.; Shaw, S. A.; Eastgate, M. D.; Baran, P. S. "Decarboxylative Alkynylation” Angew. Chem. Int. Ed. 2017, 56,11906–11910.

7. Chu, H.; Smith, J. M.; Felding, J.; Baran, P. S. “Scalable Synthesis of (–)-Thapsigargin” ACS Cent. Sci. 2017, 3, 47–51.

6. Moreno, J.; Picazo, E.; Morrill, L. A.; Smith, J. M.; Garg, N. K. “Enantioselective Total Syntheses of Akuammiline Alkaloids (+)-Strictamine, (–)-2(S)-Cathafoline, and (–)-Aspidophylline A” J. Am. Chem. Soc. 2016, 138, 1162–1165.

5. Smith, J. M.; Moreno, J.; Boal, B. W.; Garg, N. K. “Fischer Indolizations as a Strategic Platform for the Total Synthesis of Picrinine” J. Org. Chem. 2015, 80, 8954–8967.

4. Smith, J. M.; Moreno, J.; Boal, B. W.; Garg N. K. “Cascade Reactions: A Driving Force in Akuammiline Alkaloid Total Synthesis” Angew. Chem. Int. Ed. 2015, 54, 400–412.

3. Smith, J. M.; Moreno, J.; Boal, B. W.; Garg, N. K. “Total Synthesis of the Akuammiline Alkaloid Picrinine” J. Am. Chem. Soc. 2014, 136, 4504–4507.

2. Ungureanu, S.; Meadows, M.; Smith, J.; Duff, D. B.; Burgess, J. M.; Goess, B. C. “Total Synthesis of (±)- Hibiscone C” Tetrahedron Lett. 2011, 52, 1509–1511.

1. Rodrigues Jr., M. T.; Gomes, J. C.; Smith, J.; Coelho, F. “Simple and Highly Diastereoselective Access to 3,4-substituted tetrahydro-1,8-naphthyridines from Morita–Baylis–Hillman Adducts” Tetrahedron Lett. 2010, 51, 4988–4990.

Mentored Research

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