45. Synthesis and Biological Evaluation of Semi-Synthetic Albocycline Analogs

Daher, S., Franklin, K., Scherzi, T., Dunman, P., Andrade, R. Bioorg. & Med. Chem. Lett. 2020. 30 (21), 127509.

45. Synthesis of (–)-Melodinine K: A Case Study of Efficiency in Natural Product Synthesis

Walia, M.*, Teijaro, C.*, Gardner, A.*, Tran, T., Kang, J., Zhao, S., O’Connor, S., Courdavault, V., Andrade, R.B., Synthesis of (-)-Melodinine K: A Case Study of Efficiency in Natural Product Synthesis. J. Nat. Prod. 2020.

44. The Vinylogous Aldol Reaction of N-Sulfinyl Metalloenamies

Yu, P., Chatare, V., Patel, H., Debrosse, C., Andrade, R. B., The Vinylogous Aldol Reaction of N-Sulfinyl Metalloenamines. Tet. Lett. 2020, 76 (7), 130901. 

43. Synthesis and Biological Evaluation of Solithromycin Analogs Against Multidrug Resistant Pathogens

Daher, S., Jin, X., Patel, J., Freundlich, J., Buttaro, B., Andrade, R. B., Synthesis and Biological Evaluation of Solithromycin Analogs Against Multidrug Resistant Pathogens. Bioorg. Med. Chem. Lett. 2019, 29, 1386-1389.

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42. Beaufay, C., Ledoux, A., Jansen, O., Bordignon, A., Zhao, S., Teijaro, C. N., Andrade, R. B., Quetin-Leclercq, J., Frédérich, M. In vivo antimalarial and antitrypanosomal activity of strychnogucine B, a bisindole alkaloid from Strychnos icaja. Planta Med., 2018, DOI 10.1055/a-0644-2723

41. Carqueijeiro, I., Dugé de Bernonville, T., Lanoue, A., Dang, T.-T., Teijaro, C., Paetz, C., Billet, K., Mosquera, A., Oudin, A., Besseau, S., Papon, N., Glévarec, G., Atehortùa, L., Clastre, M., Giglioli-Guivarc’h, N., Schneider, B., St Pierre, B., Andrade, R., O’Connor, S., Courdavault, V. A BAHD acyltransferase catalyzing 19-O-acetylation of tabersonine derivatives in roots of Catharanthus roseus enables combinatorial synthesis of monoterpene indole alkaloids. Plant. J., 2018, 94, 469-484.

40. Chatare, V. K., Andrade, R. B. Total Synthesis of (-)-Albocyclin, Angew. Chem. Int. Ed. 2017, 56, 5905 –5911

39. Zhao, S., Andrade, R. B. Development and Scope of the Arene-Fused Domino Michael/Mannich REaction: Application to the Total Syntheses of Aspidosperma Alkaloids (-)-Aspidospermidine, (-)-Tabersonine, (-)-Vincadifformine. JOC, 2017, 82, 521−531

38. Zhao, S., Teijaro,C. N., Chen, H., Vaddypally, S. Zdilla, M., Andrade, R. B. Concise Syntheses of (-)-Sungucine, (-)-Isosungucine, and (-)-Strychnogucine B from (-)-Strychnine. Chem. Eur. J., 2016, 22, 11593–11596.

 

 

 

 

 

37. An, Y.; Doney, A. C.; Andrade, R. B.; Wheeler, S. E. Stacking Interactions between 9-Methyladenine and Heterocycles Commonly Found in Pharmaceuticals. J. Chem. Inf. Model, 2016, 56, 906-914.

36. Glassford, I., Teijaro, C. N., Daher, S. S., Weil, A., Redhu, S. K., Small, M. C., Buttaro, B., Nicholson, A. W., MacKerell, A. D. Jr., Cooperman, B. S., Andrade, R. B. Ribosome-templated azide-alkyne cycloadditions: synthesis of potent macrolide antibiotics by in situ click chemistry. JACS, 2016, 138, 3136-3144.

35. Andrade, R. B. Total Synthesis of Desmethyl Macrolide Antibiotics. Synlett, 2015, 26, 2199-2215.

34. Kokkonda, P.; Brown, K. R.; Seguin, T. J.; Wheeler, S. E.; Vaddypally, S.; Zdilla, M. J.; Andrade, R. B. Biomimetic Total Syntheses of (−)-Leucoridines A and C through the Dimerization of (−)-Dihydrovalparicine. Angew. Chem. Int. Ed., 2015, 54, 12632-12635.

33. Teijaro, C. N.; Zhao, S.; Kokkonda, P.; Andrade, R. B. Total Syntheses of  (–)-Alstolucines A, B, and F, (–)-Echitamidine, and (–)-N-Demethylalstogucine. Synthesis 2015, 47, 1547–1556.

32. Teijaro, C. N.; Munagala, S.; Zhao, S.; Sirasani, G.; Kokkonda, P.; Malofeeva, E. V.; Hopper-Borge, E.; Andrade, R. B. Synthesis and Biological Evaluation of Pentacyclic Strychnos Alkaloids as Selective Modulators of the ABCC10 (MRP7) Efflux Pump. J. Med. Chem., 2014, 57, 10383–10390.

31. Glassford, I.; Lee, M.; Wagh, B.; Velvadapu, V.; Paul, T.; Sandelin, G.; DeBrosse, C.; Klepacki, D.; Small, M.; C.; MacKerell, A. D., Jr.; Andrade, R. B. Desmethyl Macrolides: Synthesis and Evaluation of 4-Desmethyl Telithromycin. ACS Med. Chem. Lett., 2014, 5, 1021–1026.

30. Munagala, S.; Sirasani, G.; Kokkonda, P.; Phadke, M.; Krynetskaia, N.; Lu, P.; Sharom, F. J.; Chaudhury, S.; Abdulhameed, M. D. M.; Tawa, G.; Wallqvist, A.; Martinez, R.; Childers, W.; Abou-Gharbia, M.; Krynetskiy, E.; Andrade, R. B. Synthesis and evaluation of Strychnos alkaloids as MDR reversal agents for cancer cell eradication. Bioorg. Med. Chem., 2014, 22, 1148-1155.

29. Wagh, B.; Glassford, I.; Paul, T.; DeBrosse, C.; Klepacki, D.; Small, M.; C.; MacKerell, A. D., Jr.; Andrade, R. B. Desmethyl Macrolides: Synthesis and Evaluation of 4,8,10-Tridesmethyl Cethromycin. ACS Med. Chem. Lett., 2013, 4, 1114−1118.

28. Zhao, S.; Andrade, R. B. Domino Michael/Mannich/N-Alkylation Route to the Tetrahydrocarbazole Framework of Aspidosperma Alkaloids: Concise Total Syntheses of (−)-Aspidospermidine, (−)-Tabersonine, and (−)-Vincadifformine. J. Am. Chem. Soc. 2013, 135, 13334−13337

27. Sirasani, G.; Andrade, R. B. Total Synthesis of Strychnos Alkaloids Akuammicine, Strychnine, and Leuconicines A and B. In Strategies and Tactics in Organic Synthesis; Harmata, M., Ed. 2013, 9, 1−44.

26. Kaplan, J. M.; Shang, J.; Gobbo, P.; Antonello, S.; Armelao, L.; Chatare, V.; Ratner, D. M.; Andrade, R. B.; Maran, F. Confromationally Constrained Functional Peptide Monolayers for the Controlled Display of Bioactive Carbohydrate Ligands. Langmuir, 2013, 29, 8187-8192.

25. Zhao, S.; Sirasani, G.; Vaddypally, S.; Zdilla, M.; Andrade, R. B. Total Synthesis of (-)-Melotenine A. Angew. Chem. Int. Ed. 2013, 52, 8309−8311.

24. Small, M. C.; Lopes, P.; Andrade, R. B.; MacKerell, A. D., Jr. Impact of ribosomal modification on the binding of the antibiotic telithromycin using a combined Grand Canonical Monte Carlo/Molecular Dynamics simulation approach. PLoS Comput. Biol. 2013, 9, e1003113.

23. Wagh, B.; Glassford, I.; Paul, T.; DeBrosse, C.; Klepacki, D.; Small, M.; C.; MacKerell, A. D., Jr.; Andrade, R. B. Desmethyl Macrolides: Synthesis and Evaluation of 4,8-Didesmethyl Telithromycin. ACS Med. Chem. Lett., 2012, 3, 1013−1018.

22. Yu, A.; Shang, J.; Cheng, F.; Paik, B. A.; Kaplan, J. M.; Andrade, R. B.; Ratner, D. M. Biofunctional Paper via the Covalent Modification of Cellulose. Langmuir, 2012, 28, 11265–11273.

21. Velvadapu, V.; Glassford, I.; Lee, M.; Paul, T.; DeBrosse, C.; Klepacki, D.; Small, M.; C.; MacKerell, A. D., Jr.; Andrade, R. B. Desmethyl Macrolides: Synthesis and Evaluation of 4,10-Didesmethyl Telithromycin. ACS Med. Chem. Lett., 2012, 3, 211-215.

20. Shang, J.; Cheng, F.; Dubey, M.; Kaplan, J.; Rawal, M.; Jiang, X.; Newburg, D.; Sullivan, P. A.; Andrade, R. B.; Ratner, D. M. An organophosphonate strategy for functionalizing silicon photonic biosensors. Langmuir 2012, 28, 3338-3344.

19. Velvadapu, V.; Paul, T.; Wagh, B.; Glassford, I.; DeBrosse, C.; Andrade, R. B. Total Synthesis of (-)-4,8,10-Tridesmethyl Telithromycin. J. Org. Chem. 2011, 76, 7516-7527.

18. Sirasani, G.; Andrade, R. B. Total Synthesis of (-)-Leuconicine A and B. Org. Lett. 2011, 13, 4736-4737.

17. Sirasani, G.; Paul, T.; Andrade, R. B. Sequencing cross-metathesis and non-metathesis reactions to rapidly access building blocks for synthesis. Tetrahedron 2011, 67, 2197-2205.

16. Velvadapu, V.; Paul, T.; Wagh, B.; Klepacki, D.; Guvench, O.; MacKerell, A. Jr.; Andrade, R. B. Desmethyl Macrolides: Synthesis and Evaluation of 4,8,10-Tridesmethyl Telithromycin. ACS Med. Chem. Lett. 2011, 2, 68-72.

15. Sirasani, G.; Paul, T.; Dougherty, W., Jr.; Kassel, S.; Andrade, R. B. Concise Total Syntheses of (+/-)-Strychnine and (+/-)-Akuammicine. J. Org. Chem. 2010, 75, 3529–3532.

14. Sirasani, G.; Paul, T.; Andrade, R. B. Total Synthesis of (+)-Crocacin C. Bioorg. Med. Chem. 2010, 18, 3648-3655.

13. Andrade, R. B. Syntheses of the Crocacins. A Review. Org. Prep. Proced. Int. 2009, 41, 359-383.

12. Fortin, M.; Pham, K.; Kaplan, J.; Kirk, S.; Andrade, R. B. Gem-Dimethyl 4-Pentenyl Glycosides: Novel Glycosylating Agents and Anomeric Protecting Groups. Org. Lett. 2009, 11, 3594–3597.

11. Sirasani, G.; Andrade, R. B. Sequential One-Pot Cyclizations: Concise Access to the ABCE Tetracyclic Framework of Strychnos Alkaloids. Org. Lett. 2009, 11, 2085-2088.

10. Sirasani, G.; Paul, T.; Andrade, R. B. Concise asymmetric synthesis of (+)-Crocacin C. J. Org. Chem. 2008, 73, 6386-6388.

9. Paul, T.; Sirasani, G.; Andrade, R. B. One-pot sequential cross-metathesis/hydride reduction: highly stereoselective synthesis of primary (E)-allylic alcohols from terminal olefins. Tetrahedron Lett. 2008, 49, 3363-3367.

8. Andrade, R. B. Key Strategies in Glycan Synthesis Wiley Encyclopedia of Chemical Biology. 2008.

7. Velvadapu, V.; Andrade, R. B. Concise Syntheses of D-Desosamine, 2-Thiopyrimidinyl Desosamine Donors and Methyl Desosaminide Analogues from D-Glucose. Carb. Res., 2008, 343, 145–150.

6. Paul, T.; Andrade, R. B. Sequential cross-metathesis/phosphorus-based olefination: stereoselective synthesis of 2,4-dienoates. Tetrahedron Lett. 2007, 48, 5367-5370.

5. Andrade, R. B.; Martin, S. F. Formal Syntheses of (±)-Pinnaic Acid and (±)-Halichlorine. Org. Lett. 2005, 7, 5733-5735.

4. Love, K. R.; Andrade, R. B.; Seeberger, P. H. Linear Synthesis of a Protected H-Type II Pentasaccharide Using Glycosyl Phosphate Building Blocks. J. Org. Chem. 2001, 66, 8165-8176.

3. Plante, O. J.; Palmacci, E. R.; Andrade, R. B.; Seeberger, P. H. Oligosaccharide Synthesis with Glycosyl Phosphate and Dithiophosphate Triesters as Glycosylating Agents. J. Am. Chem. Soc. 2001, 123, 9545-9554.

2. Andrade, R. B.; Plante, O. J.; Melean, L. G.; Seeberger, P. H. Solid-Phase Oligosaccharide Synthesis: Preparation of Complex Structures Using a Novel Linker and Different Glycosylating Agents. Org. Lett. 1999, 1, 1811-1814.

1. Plante, O. J.; Andrade, R. B.; Seeberger, P. H. Synthesis and Use of Glycosyl Phosphates as Glycosyl Donors. Org. Lett. 1999, 1, 211-214.