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

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.

Key words

copper catalysis - photocatalysis - radical cyclization - ynamides - cyanamides - rosettacin - luotonin A - deoxyvasicinone

• 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