Network-analysis-guided synthesis of weisaconitine D and liljestrandinine

Nature

Volumn 528, Issue 7583, 2015, Pages 493-498

  Marth, C J ^a,c   Gallego, G M ^a,c,d   Lee, J C ^a,c,d   Lebold, T P ^a,c,e   Kulyk, S ^a,c,f   Kou, K G M ^a,c   Qin, J ^b   Lilien, R ^b   Sarpong, R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Cadre Research Labs   (United States)

^c UNIVERSITY OF CHICAGO LAW SCHOOL   (United States)

^d PFIZER INC   (United States)

^e JANSSEN RESEARCH AND DEVELOPMENT   (Belgium)

^f THERAVANCE INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENOID; DRUG METABOLITE; LILJESTRANDININE; ORGANIC COMPOUND; UNCLASSIFIED DRUG; WEISACONITINE D; 8-O-ETHYLACONOSINE; ACONITINE; BIOLOGICAL PRODUCT;

ALKALOID; CHEMICAL PROCESS; MOLECULAR ANALYSIS; NETWORK ANALYSIS; ORGANIC COMPOUND; SECONDARY METABOLITE;

ARTICLE; CYCLOADDITION; DIELS ALDER REACTION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; INVESTIGATIVE PROCEDURES; NETWORK ANALYSIS; PRIORITY JOURNAL; ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; INTERNET; SOFTWARE; STEREOISOMERISM; SYNTHESIS;

ACONITINE; BIOLOGICAL PRODUCTS; CHEMISTRY TECHNIQUES, SYNTHETIC; INTERNET; MOLECULAR STRUCTURE; SOFTWARE; STEREOISOMERISM;

EID: 84951281177     PISSN: 00280836     EISSN: 14764687     Source Type: Journal    
DOI: 10.1038/nature16440     Document Type: Article

References (43)

1. Nusim, S. H. (ed.) Active Pharmaceutical Ingredients: Development, Manufacturing, and Regulation 2nd edn, Vol. 205 of Drugs and the Pharmaceutical Sciences (CRC Press, 2009).
2. Schaefer, B. Natural Products in the Chemical Industry 209-518 (Springer, 2014).
3. Farina, V. Reeves, J. T., Senanayake, C. H. & Song, J. J. Asymmetric synthesis of active pharmaceutical ingredients. Chem. Rev. 106, 2734-2793 (2006).
4. dos Santos Pinheiro, E., Antunes, O. A. C. & Fortunak, J. M. D. A survey of the syntheses of active pharmaceutical ingredients for antiretroviral drug combinations critical to access in emerging nations. Antiviral Res. 79, 143-165 (2008).
5. Shenvi, R. A., O'Malley, D. P. & Baran, P. S. Chemoselectivity: the mother of invention in total synthesis. Acc. Chem. Res. 42, 530-541 (2009).
6. Hudlický, T. & Reed, J. W. The Way of Synthesis (Wiley-VCH, 2007).
7. Service, R. F. Race for molecular summits. Science 285, 184-187 (1999).
8. Negishi, E.-i. Magical power of transition metals: past, present, and future (Nobel lecture). Angew. Chem. Int. Ed. 50, 6738-6764 (2011).
9. White, M. C. C-H bond functionalization and synthesis in the 21st century: a brief history and prospectus. Synlett 23, 2746-2748 (2012).
10. Kwok, R. Five hard truths for synthetic biology. Nature 463, 288-290 (2010).
11. MacMillan, J. & Beale, M. H. Diterpene biosynthesis. Compr. Nat. Prod. Chem. 2, 217-243 (1999).
12. Koehn, F. E. & Carter, G. T. The evolving role of natural products in drug discovery. Nature Rev. Drug Discov. 4, 206-220 (2005).
13. Corey, E. J., Howe, W. J., Orf, H. W., Pensak, D. A. & Petersson, G. General methods of synthesis analysis. Strategic bond disconnections for bridged polycyclic structures. J. Am. Chem. Soc. 97, 6116-6124 (1975).
14. Chan, T. Y. K. Aconite poisoning. Clin. Toxicol. 47, 279-285 (2009).
15. Catterall, W. A. et al. Voltage-gated ion channels and gating modifier toxins. Toxicon 49, 124-141 (2007).
16. Anger, T., Madge, D. J., Mulla, M. & Riddall, D. Medicinal chemistry of neuronal voltage-gated sodium channel blockers. J. Med. Chem. 44, 115-137 (2001).
17. Vakhitova, Yu. V. et al. A study of the mechanism of the antiarrhythmic action of allapinin. Russ. J. Bioorg. Chem. 39, 92-101 (2013).
18. Nishiyama, Y., Han-ya, Y., Yokoshima, S. & Fukuyama, T. Total synthesis of (-)-lepenine. J. Am. Chem. Soc. 136, 6598-6601 (2014).
19. Shi, Y., Wilmot, J. T., Nordstrøm, L. U., Tan, D. S. & Gin, D. Y. Total synthesis, relay synthesis, and structural confirmation of the C18-norditerpenoid alkaloid neofinaconitine. J. Am. Chem. Soc. 135, 14313-14320 (2013).
20. Wiesner, K., Tsai, T. Y. R., Huber, K., Bolton, S. E. & Vlahov, R. Total synthesis of talatisamine, a delphinine type alkaloid. J. Am. Chem. Soc. 96, 4990-4992 (1974).
21. Cherney, E. C., Lopchuk, J. M., Green, J. C. & Baran, P. S. A unified approach to ent-atisane diterpenes and related alkaloids: synthesis of (-)-methyl atisenoate, (-)-isoatisine, and the hetidine skeleton. J. Am. Chem. Soc. 136, 12592-12595 (2014).
22. 1 aglycone: a hetero Diels-Alder approach. Synlett 5, 658-662 (2000).
23. Marx, J. N., Cox, J. H. & Norman, L. R. 2-Carbomethoxycyclopent-2-enone. J. Org. Chem. 37, 4489-4491 (1972).
24. 16-alphaxalone and their corresponding 17-carbonitrile analogues. Bioorg. Med. Chem. Lett. 20, 6680-6684 (2010).
25. Yokota, S. & Miyamoto, S. Insecticide. Japanese patent 2008-024670 (2008).
26. Lee, J., Kim, M., Chang, S. & Lee, H.-Y. Anhydrous hydration of nitriles to amides using aldoximes as the water source. Org. Lett. 11, 5598-5601 (2009).
27. Quideau, S. et al. Iodine-mediated and electrochemical oxidative transformations of 2-methoxy- and 2-methylphenols. ARKIVOC 2003(vi), 106-119 (2003).
28. 19-diterpenoid alkaloids via intramolecular Diels-Alder reaction followed by Wagner-Meerwein rearrangement. Tetrahedron 68, 1171-1176 (2012).
29. Fürstner, A. & Davies, P. W. Catalytic carbophilic activation: catalysis by platinum and gold π acids. Angew. Chem. Int. Ed. 46, 3410-3449 (2007).
30. Evans, D. A., Fu, G. C. & Hoveyda, A. H. Rhodium(I)-catalyzed hydroboration of olefins. The documentation of regio- and stereochemical control in cyclic and acyclic systems. J. Am. Chem. Soc. 110, 6917-6918 (1988).
31. Isayama, S. & Mukaiyama, T. Novel method for the preparation of triethylsilyl peroxides from olefins by the reaction with molecular oxygen and triethylsilane catalyzed by bis(1,3-diketonato)cobalt(II). Chem. Lett. 18, 573-576 (1989).
32. Isayama, S. An efficient method for the direct peroxygenation of various olefinic compounds with molecular oxygen and triethylsilane catalyzed by a cobalt(II) complex. Bull. Chem. Soc. Jpn 63, 1305-1310 (1990).
33. III and other single-electron transfer metals? Angew. Chem. Int. Ed. 45, 5522-5526 (2006).
34. Wiesner, K. Total synthesis of racemic talatisamine. Pure Appl. Chem. 41, 93-112 (1975).
35. Schotes, C. & Mezzetti, A. Asymmetic Diels-Alder reactions of unsaturated β-ketoesters catalyzed by chiral ruthenium PNNP complexes. J. Am. Chem. Soc. 132, 3652-3653 (2010).
36. Schotes, C., Althaus, M., Aardoom, R. & Mezzetti, A. Asymmetric Diels-Alder and Ficini reactions with alkylidene β-ketoesters catalyzed by chiral ruthenium PNNP complexes: mechanistic insight. J. Am. Chem. Soc. 134, 1331-1343 (2012).
37. Oyama, H., Orimoto, K., Niwa, T. & Nakada, M. Highly enantioselective catalytic asymmetric Mukaiyama-Michael reactions of cyclic α-alkylidene-β-oxo imides. Tetrahedr. Asymm. 26, 262-270 (2015).
38. Orimoto, K., Oyama, H., Namera, Y., Niwa, T. & Nakada, M. Catalytic asymmetric [4+2] cycloadditions and Hosomi-Sakurai reactions of α-alkylidene β-keto imides. Org. Lett. 15, 768-771 (2013).
39. Corey, E. J. & Cheng, X.-M. The Logic of Chemical Synthesis 43-44 (Wiley, 1989).
40. Hoffmann, R. W. Elements of Synthesis Planning (Springer, 2009).
41. Steinbeck, C. et al. The chemistry development kit (CDK): an open-source Java library for chemo- and bioinformatics. J. Chem. Inform. Comput. Sci. 43, 493-500 (2003).
42. Steinbeck, C. et al. Recent developments of the chemistry development kit (CDK) - an open-source Java library for chemo- and bioinformatics. Curr. Pharm. Des. 12, 2111-2120 (2006).
43. Legault, C. Y. CYLview, 1.0b. http://www.cylview.org(Université de Sherbrook, 2009).