Synthesis 2018; 50(15): 3022-3030
DOI: 10.1055/s-0037-1610134
special topic
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Photoinduced Radical Domino Cyclization of Ynamides and Cyanamides: A Unified Entry to Rosettacin, Luotonin A, and Deoxyvasicinone

Hajar Baguia
Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium   Email: gevano@ulb.ac.be
,
Christopher Deldaele
Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium   Email: gevano@ulb.ac.be
,
Eugénie Romero
Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium   Email: gevano@ulb.ac.be
,
Bastien Michelet
Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium   Email: gevano@ulb.ac.be
,
Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium   Email: gevano@ulb.ac.be
› Author Affiliations
This work was supported by the Université libre de Bruxelles (ULB) and the Fédération Wallonie-Bruxelles (ARC Consolidator 2014-2019). H. B. and C. D. acknowledge the Fonds pour la formation à la Recherche dans l’Industrie et dans l’Agriculture (F.R.I.A.) for graduate fellowships.
Further Information

Publication History

Received: 09 March 2018

Accepted after revision: 09 April 2018

Publication Date:
28 May 2018 (online)


Published as part of the Special Topic Modern Radical Methods and their Strategic Applications in Synthesis

Abstract

A general and efficient procedure for the copper-catalyzed photoinduced radical domino cyclization of ynamides and cyanamides providing an efficient access to complex tri-, tetra- and pentacyclic nitrogen heterocycles is reported. Upon visible light irradiation in the presence of catalytic amounts of [(DPEphos)(bcp)Cu]PF6 and an amine, a range of unactivated aryl and alkyl iodides were shown to be smoothly transformed to the corresponding radical species, initiating the radical domino cyclization. This procedure provides a unified entry to rosettacin, luotonin A, and deoxyvasicinone that could be efficiently prepared in a limited number of steps.

Supporting Information

 
  • References

  • 1 Gomberg M. J. Am. Chem. Soc. 1900; 22: 757
  • 2 Paneth F. Hofeditz W. Ber. Dtsch. Chem. Ges. 1929; 62: 1335
  • 3 Encyclopedia of Radicals in Chemistry, Biology and Materials . Vol. 1–4. Chatgilialoglu C. Studer A. Wiley; Chichester: 2012
  • 4 Newcomb M. In Encyclopedia of Radicals in Chemistry, Biology and Materials . Vol. 1. Chatgilialoglu C. Studer A. Wiley; Chichester: 2012: 107-124
    • 5a Beckwith AL. J. Easton CJ. Serelis AK. J. Chem. Soc., Chem. Commun. 1980; 482
    • 5b Gilmore K. Alabugin IV. Chem. Rev. 2011; 111: 6513
  • 6 Jasperse CP. Curran DP. Fevig TL. Chem. Rev. 1991; 91: 1237
  • 7 Bakuzis P. Campos OO. S. Bakuzis ML. F. J. Org. Chem. 1976; 41: 3261
  • 8 Ladlow M. Pattenden G. Tetrahedron Lett. 1985; 26: 4413
  • 9 Stork G. Baine NH. Tetrahedron Lett. 1985; 26: 5927
  • 10 Curran DP. Rackiewicz DM. J. Am. Chem. Soc. 1985; 107: 1448
  • 11 Studer A. Curran DP. Angew. Chem. Int. Ed. 2016; 55: 58
    • 12a Narayanam JM. R. Stephenson CR. J. Chem. Soc. Rev. 2011; 40: 102
    • 12b Prier CK. Rankic DA. MacMillan DW. C. Chem. Rev. 2013; 113: 5322

      For a review, see:
    • 13a Nicholls TP. Leonori D. Bissember AC. Nat. Prod. Rep. 2016; 33: 1248

    • For a review on the use of photocatalysis for the synthesis of pharmaceutical agents, see:
    • 13b Douglas JJ. Sevrin MJ. Stephenson CR. J. Org. Process Res. Dev. 2016; 20: 1134
  • 14 Romero NA. Nicewicz DA. Chem. Rev. 2016; 116: 10075

    • For reviews, see:
    • 15a Paria S. Reiser O. ChemCatChem 2014; 6: 2477
    • 15b Reiser O. Acc. Chem. Res. 2016; 49: 1990
    • 15c Boyer C. Corrigan NA. Jung K. Nguyen D. Nguyen T.-K. Adnan NN. M. Oliver S. Shanmugam S. Yeow J. Chem. Rev. 2016; 116: 1803

      For selected examples, see:
    • 16a Hernandez-Perez AC. Vlassova A. Collins SK. Org. Lett. 2012; 14: 2988
    • 16b Pirtsch M. Paria S. Matsuno T. Isobe H. Reiser O. Chem. Eur. J. 2012; 18: 7336
    • 16c Paria S. Pirtsch M. Kais V. Reiser O. Synthesis 2013; 45: 2689
    • 16d Baralle A. Fensterbank L. Goddard JP. Ollivier C. Chem. Eur. J. 2013; 19: 10809
    • 16e Hernandez-Perez AC. Collins SK. Angew. Chem. Int. Ed. 2013; 52: 12696
    • 16f Knorn M. Rawner T. Czerwieniec R. Reiser O. ACS Catal. 2015; 5: 5186
    • 16g Tang X.-J. Dolbier WR. Jr. Angew. Chem. Int. Ed. 2015; 54: 4246
    • 16h Bagal DB. Kachkovskyi G. Knorn M. Rawner T. Bhanage BM. Reiser O. Angew. Chem. Int. Ed. 2015; 54: 6999
    • 16i Fumagalli G. Rabet PT. G. Boyd S. Greaney MF. Angew. Chem. Int. Ed. 2015; 54: 11481

      For recent contributions from our group, see:
    • 17a Deldaele C. Evano G. ChemCatChem 2016; 8: 1319
    • 17b Nitelet A. Evano G. Org. Lett. 2016; 18: 1904
    • 17c Wang J. Evano G. Org. Lett. 2016; 18: 3542
    • 17d Nitelet A. Wouters J. Dewez DF. Evano G. Org. Lett. 2017; 19: 6276
    • 18a Demmer CS. Benoit E. Evano G. Org. Lett. 2016; 18: 1438
    • 18b Theunissen C. Wang J. Evano G. Chem. Sci. 2017; 8: 3465
  • 19 Michelet B. Deldaele C. Kajouj S. Moucheron C. Evano G. Org. Lett. 2017; 19: 3576
    • 20a Bailly C. Curr. Med. Chem. 2000; 7: 39
    • 20b Meng L.-H. Liao Y.-Z. Pommier Y. Curr. Top. Med. Chem. 2003; 3: 305
    • 20c Pommier Y. Nat. Rev. Cancer 2006; 6: 789
  • 21 Husain I. Mohler JL. Seigler HF. Besterman JM. Cancer. Res. 1994; 54: 539
  • 22 Wall ME. Wani MC. Cook CE. Palmer KH. McPhail AT. Sim GA. J. Am. Chem. Soc. 1966; 88: 3888
  • 23 Miyasaka T. Sawada S. Nokata K. Sugino E. Mutai M. (Yakult Honsha Corporation Ltd) US Patent 4604463, 1986
  • 24 Boehm JC. Hecht SM. Holden KG. Johnson RK. Kingsbury WD. (SmithKline Beecham Corporation) US Patent 5004758, 1991
  • 25 Jew SS. Lee HS. Kim JK. Ok KD. Cha KH. Kim MG. Lee KK. Kim JM. Kim HJ. Hah JM. (Chong Kun Dang Corporation) US Patent 6265413 B1, 2001
    • 26a Kohlhagen G. Paull KD. Cushman M. Nagafuji P. Pommier Y. Mol. Pharm. 1998; 54: 50
    • 26b Nagarajan M. Morrell A. Fort BC. Meckley MR. Antony S. Kohlhagen G. Pommier Y. Cushman M. J. Med. Chem. 2004; 47: 5651
    • 26c Morrell A. Placzek M. Parmley S. Grella B. Antony S. Pommier Y. Cushman M. J. Med. Chem. 2007; 50: 4388
    • 26d Morrell A. Antony S. Kohlhagen G. Pommier Y. Cushman M. Bioorg. Med. Chem. Lett. 2004; 14: 3659
    • 27a Fox BM. Xiao X. Antony S. Kohlhagen G. Pommier Y. Staker BL. Stewart L. Cushman M. J. Med. Chem. 2003; 46: 3275
    • 27b Cheng K. Rahier NJ. Eisenhauer BM. Gao R. Thomas SJ. Hecht SM. J. Am. Chem. Soc. 2005; 127: 838
  • 28 Lin LZ. Cordell GA. Phytochemistry 1989; 28: 1295
  • 29 For a representative example, see: Cinelli MA. Morrell A. Dexheimer TS. Scher ES. Pommier Y. Cushman M. J. Med. Chem. 2008; 51: 4609
  • 30 Ma Z.-Z. Hano Y. Nomura T. Chen Y.-J. Heterocycles 1997; 46: 541
  • 31 Ma Z.-Z. Hano Y. Nomura T. Chen Y.-J. Heterocycles 1999; 51: 1883
  • 32 Cagir A. Jones SH. Gao R. Eisenhauer BM. Hecht SM. J. Am. Chem. Soc. 2003; 125: 13628

    • For examples, see:
    • 33a Cagir A. Eisenhauer BM. Gao R. Thomas SJ. Hecht SM. Bioorg. Med. Chem. 2004; 12: 6287
    • 33b Dallavalle S. Merlini L. Beretta GL. Tinelli S. Zunino F. Bioorg. Med. Chem. Lett. 2004; 14: 5757
    • 33c Mason JJ. Bergman J. Org. Biomol. Chem. 2007; 5: 2486
    • 33d González-Ruiz V. Pascua I. Fernández-Marcelo T. Ribelles P. Bianchini G. Sridharan V. Iniesta P. Ramos MT. Olives AI. Martín MA. Menéndez JC. PLoS One 2014; 9: e95998
  • 34 Shamma M. Novak L. Tetrahedron 1969; 25: 2275
  • 35 Corey EJ. Crouse DN. Anderson JE. J. Org. Chem. 1975; 40: 2140
  • 36 Pin F. Comesse S. Sanselme M. Daïch A. J. Org. Chem. 2008; 73: 1975
    • 37a Xu X. Liu Y. Park CM. Angew. Chem. Int. Ed. 2012; 51: 9372
    • 37b Song L. Tian G. He Y. Van der Eycken E. Chem. Commun. 2017; 53: 12394
  • 38 Reddy CR. Mallesh K. Org. Lett. 2018; 20: 150
  • 39 El Blidi L. Namoune A. Bridoux A. Nimbarte VD. Lawson AM. Comesse S. Daïch A. Synthesis 2015; 47: 3583
  • 40 Li K. Ou J. Gao S. Angew. Chem. Int. Ed. 2016; 55: 14778
  • 41 For a review, see: Liang JL. Cha HC. Jahng Y. Molecules 2011; 16: 4861
  • 42 Wang H. Ganesan A. Tetrahedron Lett. 1998; 39: 9097
  • 43 Ma Z.-Z. Hano Y. Nomura T. Chen Y.-J. Heterocycles 1999; 51: 1593
  • 44 Kelly TR. Chamberland S. Silva RA. Tetrahedron Lett. 1999; 40: 2723
    • 45a Harayama T. Hori A. Serban G. Morikami Y. Matsumoto T. Abe H. Takeuchi Y. Tetrahedron 2004; 60: 10645
    • 45b Bowman WR. Elsegood MR. J. Stein T. Weaver GW. Org. Biomol. Chem. 2007; 5: 103
  • 46 Ju Y. Liu F. Li C. Org. Lett. 2009; 11: 3582
  • 47 Servais A. Azzouz M. Lopes D. Courillon C. Malacria M. Angew. Chem. Int. Ed. 2007; 46: 576

    • For representative contributions from our group on the chemistry of ynamides, see:
    • 48a Coste A. Karthikeyan G. Couty F. Evano G. Angew. Chem. Int. Ed. 2009; 48: 4381
    • 48b Jouvin K. Couty F. Evano G. Org. Lett. 2010; 12: 3272
    • 48c Fadel A. Legrand F. Evano G. Rabasso N. Adv. Synth. Catal. 2011; 353: 263
    • 48d Laouiti A. Rammah MM. Rammah MB. Marrot J. Couty F. Evano G. Org. Lett. 2012; 14: 6
    • 48e Jouvin K. Heimburger J. Evano G. Chem. Sci. 2012; 3: 756
    • 48f Laouiti A. Jouvin K. Rammah MM. Rammah MB. Evano G. Synthesis 2012; 44: 1491
    • 48g Compain G. Jouvin K. Martin-Mingot A. Evano G. Marrot J. Thibaudeau S. Chem. Commun. 2012; 48: 5196
    • 48h Gati W. Rammah MM. Rammah MB. Couty F. Evano G. J. Am. Chem. Soc. 2012; 134: 9078
    • 48i Gati W. Couty F. Boubaker T. Rammah MM. Rammah MB. Evano G. Org. Lett. 2013; 15: 3122
    • 48j Laub HA. Evano G. Mayr H. Angew. Chem. Int. Ed. 2014; 53: 4968
    • 48k Laouiti A. Couty F. Marrot J. Boubaker T. Rammah MM. Rammah MB. Evano G. Org. Lett. 2014; 16: 2252
    • 48l Theunissen C. Metayer B. Henry N. Compain G. Marrot J. Martin-Mingot A. Thibaudeau S. Evano G. J. Am. Chem. Soc. 2014; 136: 12528
    • 48m Lecomte M. Evano G. Angew. Chem. Int. Ed. 2016; 55: 4547
    • 48n Demmer CS. Evano G. Synlett 2016; 27: 1873
    • 48o Evano G. Blanchard N. Compain G. Coste A. Demmer CS. Gati W. Guissart C. Heimburger J. Henry N. Jouvin K. Karthikeyan G. Laouiti A. Lecomte M. Martin-Mingot A. Métayer B. Michelet B. Nitelet A. Theunissen C. Thibaudeau S. Wang J. Zarca M. Zhang C. Chem. Lett. 2016; 45: 574
    • 48p Vercruysse S. Jouvin K. Riant O. Evano G. Synthesis 2016; 48: 3373
  • 49 Marion F. Courillon C. Malacria M. Org. Lett. 2003; 5: 5095
  • 50 Han Y.-Y. Jiang H. Wang R. Yu S. J. Org. Chem. 2016; 81: 7276
  • 51 Hu J. Wang J. Nguyen TH. Zheng N. Beilstein J. Org. Chem. 2013; 9: 1977
  • 52 Witulski B. Stengel T. Angew. Chem. Int. Ed. 1998; 37: 489
  • 53 Arora A. Weaver JD. Org. Lett. 2016; 18: 3996
  • 54 Amin AH. Mehta DR. Nature 1959; 183: 1317
  • 55 Al-Shamma A. Drake S. Flynn DL. Mitscher LA. Park YH. Rao GS. R. Simpson A. Swayze JK. Veysoglu T. Wu ST. S. J. Nat. Prod. 1981; 44: 745

    • For representative syntheses, see:
    • 56a Mori M. Kobayashi H. Kimura M. Ban Y. Heterocycles 1985; 23: 2803
    • 56b Takeuchi H. Hagiwara S. Eguchi S. Tetrahedron 1989; 45: 6375
    • 56c Akazome M. Kondo T. Watanabe Y. J. Org. Chem. 1993; 58: 310
    • 56d Mori M. Kobayashi H. Kimura M. Ban Y. Heterocycles 1997; 46: 541
    • 56e Mhaske SB. Argade NP. J. Org. Chem. 2001; 66: 9038
    • 56f Lee ES. Park J.-G. Jahng Y. Tetrahedron Lett. 2003; 44: 1883
    • 56g Liu J.-F. Ye P. Sprague K. Sargent K. Yohannes D. Baldino CM. Wilson CJ. Ng S.-C. Org. Lett. 2005; 7: 3363
    • 56h Gil C. Bräse S. Chem. Eur. J. 2005; 11: 2680
    • 56i Hamid A. Elomri A. Daich A. Tetrahedron Lett. 2006; 47: 1777
    • 56j Bowman WR. Elsegood MR. J. Stein T. Weaver GW. Org. Biomol. Chem. 2007; 5: 103
    • 56k Potewar TM. Ingale SA. Srinivasan KV. ARKIVOC 2008; (xiv): 100
    • 56l Zhang C. De C K. Mal R. Seidel D. J. Am. Chem. Soc. 2008; 130: 416
    • 56m Fang J. Zhou J. Org. Biomol. Chem. 2012; 10: 2389
    • 56n Larraufie M.-H. Malacria M. Courillon C. Ollivier C. Fensterbank L. Lacôte E. Tetrahedron 2013; 69: 7699
  • 57 Kotani S. Osakama K. Sugiura M. Nakajima M. Org. Lett. 2011; 13: 3968
  • 58 Luo W.-K. Shi X. Zhou W. Yang L. Org. Lett. 2016; 18: 2036