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

Abstract

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

Publication History

Received: 31 July 2020

Accepted after revision: 29 September 2020

Article published online:
09 November 2020

• 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