Recent Advances in One-Pot Enyne Metathesis Processes for the Preparation of Biologically and Medicinally Relevant Compounds

Enyne metathesis reactions are powerful tools for the preparation of a wide range of synthetic and natural chemical substances with increasing efficiency and environmental sustainability. The driving force of the reaction is the formation of a stable conjugated system, i.e., a diene, which through further functionalization steps can be used for the construction of skeletally complex molecular architectures. These concepts are exploited to design cascade reaction sequences, where multiple rings can be formed in a one-pot fashion by combining metathetic protocols with various chemical transformations. The strong correlation between synthetic organic chemistry and medicinal chemistry prompted us to review the most notable approaches for the synthesis of biologically relevant compounds via enyne metathesis-based one-pot processes. With the aim to provide a modern and practical overview, by taking into consideration the scientific literature on this topic, we have focused the majority of our attention on the research performed in the last decade. This review covers the literature from 2003 to 2020.

1 Introduction

2 Ethylene-Mediated Processes

3 RCEYM/CM and CEYM/RCM Processes

4 Enyne Metathesis/Diels–Alder-Based Processes

5 RCM of Dienynes

6 RCM of Tethered Dienynes

7 Relay Metathesis

8 Ring-Rearrangement Metathesis

9 RCEYM/Transition-Metal-Catalyzed C–C Bond-Forming Processes

10 Conclusions

11 List of Acronyms

Key words

enyne metathesis - dienynes - one-pot - ruthenium catalysis - natural products - ring-closing - cascade/domino reactions - biologically active

Volltext

Referenzen

References

1a Hughes D, Wheeler P, Ene D. Org. Process Res. Dev. 2017; 21: 1938
1b Yu M, Lou S, Gonzalez-Bobes F. Org. Process Res. Dev. 2018; 22: 918
1c Lecourt C, Dhambri S, Allievi L, Sanogo Y, Zeghbib N, Ben Othman R, Lannou M.-I, Sorin G, Ardisson J. Nat. Prod. Rep. 2018; 35: 105
1d Ogba OM, Warner NC, O’Leary DJ, Grubbs RH. Chem. Soc. Rev. 2018; 47: 4510
1e Prunet J. Eur. J. Org. Chem. 2011; 3634
1f Cheng-Sánchez I, Sarabia F. Synthesis 2018; 50: 3749

2a Trost BM. Science 1991; 254: 1471
2b Trost BM. Angew. Chem. Int. Ed. 1995; 34: 259

3a Diver ST, Giessert AJ. Chem. Rev. 2004; 104: 1317
3b Li J, Lee D. Eur. J. Org. Chem. 2011; 4269
3c Dragutan V, Dragutan I. J. Organomet. Chem. 2006; 691: 5129
3d Kotha S, Meshram M, Tiwari A. Chem. Soc. Rev. 2009; 38: 2065
3e Holub N, Blechert S. Chem. Asian J. 2007; 2: 1064
3f Mori M. Adv. Synth. Catal. 2007; 349: 121
3g Roscales S, Plumet J. Nat. Prod. Commun. 2017; 12: 713
3h Mori M. Materials 2010; 3: 2087
3i Aldegunde MJ, García-Fandiño R, Castedo L, Granja JR. Chem. Eur. J. 2007; 13: 5135
3j Kotha S, Chavan AS, Goyal D. ACS Omega 2019; 4: 22261
3k Dragutan I, Dragutan V, Demonceau A, Delaude L. Curr. Org. Chem. 2013; 17: 2678
3l Han J.-C, Li C.-C. Chem. Rec. 2017; 17: 499

4a Fürstner A, Davies PW. Chem. Commun. 2005; 2307
4b Zhang W, Moore JS. Adv. Synth. Catal. 2007; 349: 93
4c Schwab P, Grubbs RH, Ziller JW. J. Am. Chem. Soc. 1996; 118: 100
4d Schwab P, France MB, Ziller JW, Grubbs RH. Angew. Chem. Int. Ed. 1995; 34: 2039

5a Huang J.-K, Stevens ED, Nolan SP, Petersen JL. J. Am. Chem. Soc. 1999; 121: 2674
5b Scholl M, Trnka TM, Morgan JP, Grubbs RH. Tetrahedron Lett. 1999; 40: 2247
5c Ackermann L, Fürstner A, Weskamp T, Kohl FJ, Herrmann WA. Tetrahedron Lett. 1999; 40: 4787
5d Scholl M, Ding S, Lee CW, Grubbs RH. Org. Lett. 1999; 1: 953

6a Kingsbury JS, Harrity JP. A, Bonitatebus PJ, Hoveyda AH. J. Am. Chem. Soc. 1999; 121: 791
6b Garber SB, Kingsbury JS, Gray BL, Hoveyda AH. J. Am. Chem. Soc. 2000; 122: 8168
6c Gessler S, Randl S, Blechert S. Tetrahedron Lett. 2000; 41: 9973
6d Wakamatsu H, Blechert S. Angew. Chem. Int. Ed. 2002; 41: 2403

7a Michrowska A, Bujok R, Harutyunyan S, Sashuk V, Dolgonos G, Grela K. J. Am. Chem. Soc. 2004; 126: 9318
7b Grela K, Harutyunyan S, Michrowska A. Angew. Chem. Int. Ed. 2002; 41: 4038

8 Zhan Z.-Y. US20070043180A1, 2007
9 Love JA, Morgan JP, Trnka TM, Grubbs RH. Angew. Chem. Int. Ed. 2002; 41: 4035
10 Kinoshita A, Mori M. Synlett 1994; 1020
11 Hérisson PJ, Chauvin Y. Makromol. Chem. 1971; 141: 161

12a Sohn J.-H, Kim KH, Lee H.-Y, No ZS, Ihee H. J. Am. Chem. Soc. 2008; 130: 16506
12b Grotevendt AG. D, Lummiss JA. M, Mastronardi ML, Fogg DE. J. Am. Chem. Soc. 2011; 133: 15918
12c Diver ST, Kulkarni AA, Clark DA, Peppers BP. J. Am. Chem. Soc. 2007; 129: 5832
12d Hoye TR, Donaldson SM, Vos TJ. Org. Lett. 1999; 1: 277
12e Schramm MP, Reddy DS, Kozmin SA. Angew. Chem. Int. Ed. 2001; 40: 4274
12f Galan BR, Giessert AJ, Keister JB, Diver ST. J. Am. Chem. Soc. 2005; 127: 5762

13a Katz TJ, Sivavec TM. J. Am. Chem. Soc. 1985; 107: 737
13b Sivavec TM, Katz TJ, Chiang MY, Yang GX.-Q. Organometallics 1989; 8: 1620
13c Katz TJ, Yang GX.-Q. Tetrahedron Lett. 1991; 32: 5895

14a Hayashi Y. Chem. Sci. 2016; 7: 866
14b Clarke PA, Santos S, Martin WH. C. Green Chem. 2007; 9: 438
14c Vaxelaire C, Winter P, Christmann M. Angew. Chem. Int. Ed. 2011; 50: 3605

15 Mori M, Sakakibara N, Kinoshita A. J. Org. Chem. 1998; 63: 6082
16 Diver ST, Clark JR. In Comprehensive Organic Synthesis, 2nd ed., Vol. 5. Knochel P, Molander GA. Elsevier; Amsterdam: 2014: 1302

17a Kim CH, An HJ, Shin WK, Yu W, Woo SK, Jung SK, Lee E. Angew. Chem. Int. Ed. 2006; 45: 8019
17b Kim CH, An HJ, Shin WK, Yu W, Woo SK, Jung SK, Lee E. Chem. Asian J. 2008; 3: 1523

18 Betkekar VV, Panda S, Kaliappan KP. Org. Lett. 2012; 14: 198

19a Serra M, Tambini SM, Di Giacomo M, Peviani EG, Belvisi L, Colombo L. Eur. J. Org. Chem. 2015; 7557
19b Serra M, Peviani EG, Bernardi E, Colombo L. J. Org. Chem. 2017; 82: 11091
19c Serra M, Bernardi E, De Lorenzi E, Colombo L. J. Org. Chem. 2019; 84: 15726
19d Bernardi E, Serra M, De Lorenzi E, Carraro M, Colombo L. J. Org. Chem. 2020; 24: 3568

20 St-Cyr DJ, García-Ramos Y, Doan N.-D, Lubell WD. Peptidomimetics I . In Topics in Heterocyclic Chemistry, Vol. 48. Lubell WD. Springer; Germany: 2017: 125

21a Arosio D, Belvisi L, Colombo L, Colombo M, Invernizzi D, Manzoni L, Potenza D, Serra M, Castorina M, Pisano C, Scolastico C. ChemMedChem 2008; 3: 1589
21b Paolillo M, Russo M, Serra M, Colombo L, Schinelli S. Mini-Rev. Med. Chem. 2009; 9: 1439
21c Paolillo M, Serra M, Schinelli S. Pharmacol. Res. 2016; 113: 55

22a Nolan SP, Clavier H. Chem. Soc. Rev. 2010; 39: 3305
22b Nuñez-Zarur F, Solans-Monfort X, Rodríguez-Santiago L, Pleixats R, Sodupe M. Chem. Eur. J. 2011; 17: 7506

23 Royer F, Vilain C, Elkaïm L, Grimaud L. Org. Lett. 2003; 5: 2007
24 Kummer DA, Brenneman JB, Martin SF. Org. Lett. 2005; 7: 4621
25 Boyer FD, Hanna I. Org. Lett. 2007; 9: 2293
26 Boyer FD, Dubois J, Thoret S, Dau ME. T. H, Hanna I. Bioorg. Chem. 2010; 38: 149
27 Feng J, Lei X, Bao R, Li Y, Xiao C, Hu L, Tang Y. Angew. Chem. Int. Ed. 2017; 56: 16323
28 Cho J, Yun ML, Kim D, Kim S. J. Org. Chem. 2009; 74: 3900
29 Kwon Y, Song J, Bae H, Kim WJ, Lee JY, Han GH, Lee SK, Kim S. Mar. Drugs 2015; 13: 824

30a Serra M, Bernardi E, Marrubini G, De Lorenzi E, Colombo L. Eur. J. Org. Chem. 2019; 732
30b Serra M, Bernardi E, Marrubini G, Colombo L. Eur. J. Org. Chem. 2017; 2964

31a Paolillo M, Colombo L, Serra M, Belvisi L, Papetti A, Ciusani E, Comincini S, Schinelli S. Cells 2019; 8: 1434
31b Paolillo M, Galiazzo MC, Daga A, Ciusani E, Serra M, Colombo L, Schinelli S. Int. J. Oncol. 2018; 53: 2683
31c Russo MA, Paolillo M, Sanchez-Hernandez Y, Curti D, Ciusani E, Serra M, Colombo L, Schinelli S. Int. J. Oncol. 2013; 42: 83

32 Lee HY, Kim HY, Tae H, Kim BG, Lee J. Org. Lett. 2003; 5: 3439
33 Kurhade SE, Sanchawala AI, Ravikumar V, Bhuniya D, Reddy DS. Org. Lett. 2011; 13: 3690
34 Grafton MW, Farrugia LJ, Senn HM, Sutherland A. Chem. Commun. 2012; 48: 7994
35 Mostafa MA. B, Grafton MW, Wilson C, Sutherland A. Org. Biomol. Chem. 2016; 14: 3284
36 Grafton MW, Johnson SA, Farrugia LJ, Sutherland A. Tetrahedron 2014; 70: 7133
37 Mostafa MA. B, McMillan AE, Sutherland A. Org. Biomol. Chem. 2017; 15: 3035
38 Tiong EA, Rivalti D, Williams BM, Gleason JL. Angew. Chem. Int. Ed. 2013; 52: 3442
39 Kashinath K, Jadhav PD, Reddy DS. Org. Biomol. Chem. 2014; 12: 4098
40 Betkekar VV, Sayyad AA, Kaliappan KP. Org. Lett. 2014; 16: 5540
41 Feng C, Tian XL, Zhou J, Xiang SK, Yu WH, Wang BQ, Hu P, Redshaw C, Zhao KQ. Org. Biomol. Chem. 2014; 12: 6977
42 Kim S.-H, Bowden N, Grubbs RH. J. Am. Chem. Soc. 1994; 116: 10801
43 For a review on group-selective ring-closing enyne metathesis, see: Maifeld SV, Lee D. Chem. Eur. J. 2005; 11: 6118
44 Boyer FD, Hanna I, Ricard L. Org. Lett. 2004; 6: 1817
45 Honda T, Namiki H, Kaneda K, Mizutani H. Org. Lett. 2004; 6: 87
46 Honda T, Namiki H, Watanabe M, Mizutani H. Tetrahedron Lett. 2004; 45: 5211
47 Kaliappan KP, Nandurdikar RS. Org. Biomol. Chem. 2005; 3: 3613
48 Shimizu K, Takimoto M, Sato Y, Mori M. J. Organomet. Chem. 2006; 691: 5466
49 Niethe A, Fischer D, Blechert S. J. Org. Chem. 2008; 73: 3088
50 Garcia-Fandiño R, Codesido EM, Sobarzo-Sánchez E, Castedo L, Granja JR. Org. Lett. 2004; 6: 193
51 Aldegunde MJ, Castedo L, Granja JR. Org. Lett. 2008; 10: 3789
52 Pérez-Estrada S, Sayar N, Granja JR. Org. Chem. Front. 2016; 3: 1331
53 Letort A, Aouzal R, Ma C, Long DL, Prunet J. Org. Lett. 2014; 16: 3300
54 Ma C, Letort A, Aouzal R, Wilkes A, Maiti G, Farrugia LJ, Ricard L, Prunet J. Chem. Eur. J. 2016; 22: 6891
55 Letort A, Long DL, Prunet J. J. Org. Chem. 2016; 81: 12318
56 Schubert M, Metz P. Angew. Chem. Int. Ed. 2011; 50: 2954
57 Wang Y, Jäger A, Gruner M, Lübken T, Metz P. Angew. Chem. Int. Ed. 2017; 56: 15861
58 Chang L, Jiang H, Fu J, Liu B, Li CC, Yang Z. J. Org. Chem. 2012; 77: 3609
59 Li K, Wang C, Yin G, Gao S. Org. Biomol. Chem. 2013; 11: 7550

60a Oguri H, Hiruma T, Yamagishi Y, Oikawa H, Ishiyama A, Otoguro K, Yamada H, Omuraz S. J. Am. Chem. Soc. 2011; 133: 7096
60b Oguri H. Chem. Rec. 2016; 16: 652

61 Ramharter J, Weinstabl H, Mulzer J. J. Am. Chem. Soc. 2010; 132: 14338
62 Shi L, He Y, Gong J, Yang Z. Chem. Commun. 2020; 56: 531
63 Otero-Fraga J, Granja JR. Org. Chem. Front. 2017; 4: 460
64 Kim YJ, Lee D. Org. Lett. 2006; 8: 5219
65 Mukherjee S, Lee D. Org. Lett. 2009; 11: 2916
66 Movassaghi M, Piizzi G, Siegel DS, Piersanti G. Angew. Chem. Int. Ed. 2006; 45: 5859

67a Siegel DS, Piizzi G, Piersanti G, Movassaghi M. J. Org. Chem. 2009; 74: 9292
67b Movassaghi M, Piizzi G, Siegel DS, Piersanti G. Tetrahedron Lett. 2009; 50: 5489

68 Hoye TR, Jeffrey CS, Tennakoon MA, Wang J, Zhao H. J. Am. Chem. Soc. 2004; 126: 10210
69 For a review of relay ring-closing metathesis, see: Wallace DJ. Angew. Chem. Int. Ed. 2005; 44: 1912
70 Li J, Park S, Miller RL, Lee D. Org. Lett. 2009; 11: 571
71 Li J, Lee D. Chem. Asian J. 2010; 5: 1298
72 Wei H, Qiao C, Liu G, Yang Z, Li CC. Angew. Chem. Int. Ed. 2013; 52: 620
73 Posner GH, Babiak KA, Loomis GL, Frazee WJ, Mittal RD, Karle IL. J. Am. Chem. Soc. 1980; 102: 7498
74 For general information on bilharziasis, see (accessed Oct 29, 2020): https://www.who.int/ith/diseases/schistosomiasis/en
75 Knüppel S, Rogachev VO, Metz P. Eur. J. Org. Chem. 2010; 32: 6145
76 Barthel A, Kaden F, Jäger A, Metz P. Org. Lett. 2016; 18: 3298
77 Wang Y, Darweesh AF, Zimdars P, Metz P. Beilstein J. Org. Chem. 2019; 15: 858
78 Kress S, Weckesser J, Schulz SR, Blechert S. Eur. J. Org. Chem. 2013; 7: 1346
79 Hanessian S. In Natural Products in Medicinal Chemistry, Vol. 60. Mannhold R, Kubinyi H, Folkers G. Wiley-VCH; Weinheim: 2014
80 Lin M, Cui H, Hua Y, Zhang Y. Org. Chem. Front. 2019; 6: 2771
81 Datta R, Ghosh S. Beilstein J. Org. Chem. 2018; 14: 2708
82 Lee JM, Na Y, Han H, Chan S. Chem. Soc. Rev. 2004; 33: 302
83 Raikar SN, Malinakova HC. J. Org. Chem. 2013; 78: 3832
84 Trost BM, Machacek MR, Faulk BD. J. Am. Chem. Soc. 2006; 128: 6745