Pyrroles as Dienes in (4+3) Cycloadditions

Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

This short review summarizes the examples to date of successful (4+3) cycloadditions, including formal (4+3) cycloadditions, where pyrrole derivatives reacted as the diene component, to provide aza-bridged bicyclic and polycyclic adducts.

1 Introduction

2 Unsubstituted Pyrroles as Dienes in (4+3) Cycloadditions

3 C-Substituted Pyrroles as Dienes in (4+3) Cycloadditions

4 Intramolecular Pyrrole (4+3) Cycloadditions

5 Conclusions

Key words

(4+3) cycloadditions - pyrroles - oxyallylic cations - tropanes - alkaloids - aza-bridge - cyclopropanation - Cope rearrangement

• References

• 1a Dias DA, Urban S, Roessner U. Metabolites 2012; 2: 303
• 1b Shen B. Cell 2015; 163: 1297
• 1c Bernardini S, Tiezzi A, Laghezza Masci V, Ovidi E. Nat. Prod. Res. 2018; 32: 1926
• 2 Hesse M. Alkaloids. Nature’s Curse or Blessing? . Wiley-VCH; Weinheim: 2002

For reviews on the tropane alkaloids, see:
• 3a Fodor G, Dharanipragada R. Nat. Prod. Rep. 1994; 11: 443
• 3b O’Hagan D. Nat. Prod. Rep. 1997; 14: 637
• 3c O’Hagan D. Nat. Prod. Rep. 2000; 17: 435
• 3d Lounasmaa M. In The Alkaloids: Chemistry and Pharmacology, Vol. 33. Brossi A. Academic Press; New York: 1988: 1
• 3e Lounasmaa M, Tamminen T. In The Tropane Alkaloids in Alkaloid, Vol. 44. Academic Press; New York: 1993: 1
• 3f Schulte ML, Lindsley CW. In Bioactive Heterocyclic Compound Classes: Pharmaceuticals . Lamberth JD. C. Wiley-VCH; Weinheim: 2012: 23
• 4a Gaedcke F. Arch. Pharm. (Weinheim, Ger.) 1855; 132: 141
• 4b Pomara C, Cassano T, D’Errico S, Bello S, Romano AD, Riezzo I, Serviddio G. Curr. Med. Chem. 2012; 19: 5647
• 5a Silva GL, Cui B, Cha’vez D, You M, Chai H.-B, Rasoanaivo P, Lynn SM, O’Neill MJ, Lewis JA, Besterman JM. J. Nat. Prod. 2001; 64: 1514
• 5b Mi Q, Cui B, Lantvit D, Reyes-Lim E, Chai H, Pezzuto JM, Kinghorn AD, Swanson SM. Anticancer Res. 2003; 23: 3607
• 5c Mi Q, Cui B, Silva GL, Lantvit D, Lim E, Chai H, You M, Hollingshead MG, Mayo JG, Kinghorn AD. Cancer Res. 2001; 61: 4030
• 6a Ladenburg A. Justus Liebigs Ann. Chem. 1881; 206: 274
• 6b Ullrich SF, Hagels H, Kayser O. Phytochem. Rev. 2017; 16: 333
• 7a Mein HF. G. Ann. Pharm. (Lemgo, Ger.) 1833; 6: 67
• 7b Geiger PL, Hesse H. Ann. Pharm. (Lemgo, Ger.) 1833; 5: 4
• 8 Corey EJ, Czako B, Kürti L. Molecules and Medicine . John Wiley & Sons; Hoboken: 2007
• 9 Grynkiewicz G, Gadzikowska M. Pharmacol. Rep. 2008; 60: 439
• 10a Ritchie E, Taylor WC. In The Alkaloids: Chemistry and Physiology, Vol. 9. Manske RH. F. Academic Press; New York: 1967: 529
• 10b Irie H, Masaki N, Ohno K, Osaki K, Taga T, Uyeo S. J. Chem. Soc. D 1970; 1066
• 10c Sakata K, Aoki K, Chang C.-F, Sakurai A, Tamura S, Murakoshi S. Agric. Biol. Chem. 1978; 42: 457
• 10d Ke C, He ZS, Yang YP, Ye Y. Chin. Chem. Lett. 2003; 14: 173
• 10e Pilli RA, Ferreira de Oliveira MC. Nat. Prod. Rep. 2000; 17: 117
• 10f Pilli RA, Rosso GB, Ferreira de Oliveira MC. Nat. Prod. Rep. 2010; 27: 1908
• 11 For a review on a range of synthetic strategies toward the tropanes, see: Pollini GP, Benetti S, De Risi C, Zanirato V. Chem. Rev. 2006; 106: 2434

For reviews on the classical (4+3) cycloaddition, see:
• 12a Yin Z, He Y, Chiu P. Chem. Soc. Rev. 2018; 47: 8881
• 12b Jones DE, Harmata M. In Methods and Applications of Cycloaddition Reactions in Organic Syntheses . Nishiwaki N. John Wiley & Sons; Hoboken: 2014: 599
• 12c Lam SY. Y, Chiu P. Methods and Applications of Cycloaddition Reactions in Organic Syntheses . Nishiwaki N. John Wiley & Sons; Hoboken: 2014: 565
• 12d Lohse AG, Hsung RP. Chem. Eur. J. 2011; 17: 3812
• 12e Harmata M. Chem. Commun. 2010; 8904
• 12f Harmata M. Chem. Commun. 2010; 8886
• 12g Harmata M. Adv. Synth. Catal. 2006; 348: 2297
• 12h Huang J, Hsung RP. Chemtracts 2005; 18: 207
• 12i Harmata M. Acc. Chem. Res. 2001; 34: 595
• 12j Cha JK, Oh J. Curr. Org. Chem. 1998; 2: 217
• 12k Harmata M. In Advances in Cycloaddition, Vol. 4. Lautens M. JAI Press; Greenwich: 1997: 4186
• 12l West FG. In Advances in Cycloaddition, Vol. 4. Lautens M. JAI Press; Greenwich: 1997: 140
• 12m Harmata M. Tetrahedron 1997; 53: 6235
• 12n Padwa A, Schoffstall A. In Advances in Cycloaddition, Vol. 2. Curran DP. JAI Press; Greenwich: 1990: 189
• 12o Harmata M. Recent Res. Dev. Org. Chem. 1997; 1: 523
• 12p Rigby JH, Pigge FC. Org. React. 1997; 51: 351
• 12q Mann J. Tetrahedron 1986; 42: 4611
• 12r Hoffmann HM. R. Angew. Chem., Int. Ed. Engl. 1984; 23: 1
• 12s Noyori R, Hayakawa Y. Org. React. 1983; 29: 163
• 12t Hoffmann HM. R. Angew. Chem., Int. Ed. Engl. 1973; 12: 819
• 13 Lubell W, Saint-Cyr D, Dufour-Gallant J, Hopewell R, Boutard N, Kassem T, Dorr A, Zelli R. In Science of Synthesis Updates . Thieme; Stuttgart: 2013: 157
• 14 Cramer CJ, Barrows SE. J. Phys. Org. Chem. 2000; 13: 176
• 15 Cramer CJ, Barrows SE. J. Org. Chem. 1998; 63: 5523
• 16 Jolicoeur B, Chapman EE, Thompson A, Lubell WD. Tetrahedron 2006; 62: 11531
• 17 Rawson DI, Carpenter BK, Hoffmann HM. R. J. Am. Chem. Soc. 1979; 101: 1786

For reviews on the cyclopropanation/Cope rearrangement cascade reaction, see ref. 12a and:
• 18a Cheng Q.-Q, Deng Y, Lankelma M, Doyle MP. Chem. Soc. Rev. 2017; 46: 5425
• 18b Thumar NJ, Wei QH, Hu WH. Adv. Organomet. Chem. 2016; 66: 33
• 18c Davies HM. L, Denton JR. Chem. Soc. Rev. 2009; 38: 3061
• 18d Davies HM. L. Tetrahedron 1993; 49: 5203
• 19 Fort AW. J. Am. Chem. Soc. 1962; 84: 4979
• 20a Cowling AP, Mann J, Usmani AA. J. Chem. Soc., Perkin Trans. 1 1981; 2116
• 20b MaGee DI, Godineau E, Thornton PD, Walters MA, Sponholtz DJ. Eur. J. Org. Chem. 2006; 3667
• 21 Jin S.-j, Choi J.-R, Oh J, Lee D, Cha JK. J. Am. Chem. Soc. 1995; 117: 10914
• 22 Richardson RD, Holland EJ, Carpenter BK. Nat. Chem. 2011; 3: 301
• 23 Kende AS, Huang H. Tetrahedron Lett. 1997; 38: 3353
• 24 Jeffrey CS, Anumandla D, Carson CR. Org. Lett. 2012; 14: 5764
• 25a Cookson RC, Nye MJ, Subrahmanyam G. J. Chem. Soc. C 1967; 473
• 25b Noyori R, Makino S, Takaya H. J. Am. Chem. Soc. 1971; 93: 1272
• 26 Hoffmann HM. R, Clemens KE, Smithers RH. J. Am. Chem. Soc. 1972; 94: 3940
• 27 Montaña AM, Grima PM. Tetrahedron Lett. 2001; 42: 7809
• 28 Montaña AM, Grima PM. Synth. Commun. 2003; 33: 265
• 29 Fierz G, Chidgey R, Hoffmann HM. R. Angew. Chem., Int. Ed. Engl. 1974; 13: 410
• 30 Cowling AP, Mann J. J. Chem. Soc., Perkin Trans. 1 1978; 1564
• 31 Sarhan AE.-W. A. O. Monatsh. Chem. 1999; 130: 563
• 32 Only one other successful example for engaging 1a in a (4+3) cycloaddition was with a cyclopropanone, although the yield was not reported: Turro NJ, Edelson SS, Williams JR, Darling TR, Hammond WB. J. Am. Chem. Soc. 1969; 91: 2283
• 33 Takaya H, Makino S, Hayakawa Y, Noyori R. J. Am. Chem. Soc. 1978; 100: 1765
• 34 Noyori R, Makino S, Baba Y, Hayakawa Y. Tetrahedron Lett. 1974; 15: 1049
• 35a Noyori R, Baba Y, Hayakawa Y. J. Am. Chem. Soc. 1974; 96: 3336
• 35b Hayakawa Y, Baba Y, Makino S, Noyori R. J. Am. Chem. Soc. 1978; 100: 1786
• 36a Mihovilovic MD, Grötzl B, Kandioller W, Snajdrova R, Muskotál A, Bianchi DA, Stanetty P. Adv. Synth. Catal. 2006; 348: 463
• 36b Xia Y, Chackalamannil S, Greenlee WJ, Jayne C, Neustadt B, Stamford A, Vaccaro H, Xu X, Baker H, O’Neill K, Woods M, Hawes B, Kowalski T. Bioorg. Med. Chem. Lett. 2011; 21: 3290
• 37 Reinecke J, Hoffmann HM. R. Chem. Eur. J. 1995; 1: 368
• 38 Hoffmann HM. R, Iqbal MN. Tetrahedron Lett. 1975; 16: 4487
• 39 Mann J, de Almeida Barbosa L.-C. J. Chem. Soc., Perkin Trans. 1 1992; 787
• 40 Kim KD, Park YH. J. Korean Chem. Soc. 1996; 40: 590
• 41 Paparin J.-L, Crévisy C, Toupet L, Grée R. Eur. J. Org. Chem. 2000; 3909
• 42 Paparin J.-L, Crévisy C, Grée R. Tetrahedron Lett. 2000; 41: 2343
• 43 Hodgson DM, Shelton RE, Moss TA, Dekhane M. Org. Lett. 2010; 12: 2834
• 44 Cramer N, Laschat S, Baro A, Frey W. Synlett 2003; 2175
• 45 Kulkarni K, Zhao AY, Purcell AW, Perlmutter P. Synlett 2008; 2209
• 46 Vlahovic S, Schädel N, Tussetschläger S, Laschat S. Eur. J. Org. Chem. 2013; 1580
• 47 Smits R, Fischer S, Hiller A, Deuther-Conrad W, Wenzel B, Patt M, Cumming P, Steinbach J, Sabri O, Brust P, Hoepping A. Bioorg. Med. Chem. 2014; 22: 804
• 48 Niethe A, Blechert S. Heterocycles 2007; 74: 803
• 49 Hodgson DM, Paruch E. Tetrahedron 2004; 60: 5185
• 50 Affolter O, Baro A, Laschat S, Fischer P. Z. Naturforsch. B 2007; 62: 82
• 51 Fuchigami R, Namba K, Tanino K. Tetrahedron Lett. 2012; 53: 5725
• 52 Shibata M, Fuchigami R, Kotaka R, Namba K, Tanino K. Tetrahedron 2015; 71: 4495
• 53 Antoline JE, Hsung RP, Huang J, Song Z, Li G. Org. Lett. 2007; 9: 1275
• 54 He S, Hsung RP, Presser WR, Ma Z.-X, Haugen BJ. Org. Lett. 2014; 16: 2180
• 55a Davies HM. L, Huby NJ. S. Tetrahedron Lett. 1992; 33: 6935
• 55b Davies HM. L, Matasi JJ, Hodges LM, Huby NJ. S, Thornley C, Kong N, Houser JH. J. Org. Chem. 1997; 62: 1095
• 56 Davies HM. L, Young WB, Smith HD. Tetrahedron Lett. 1989; 30: 4653
• 57 Davies HM. L, Saikali E, Young WB. J. Org. Chem. 1991; 56: 5696
• 58 Nocquet P.-A, Opatz T. Eur. J. Org. Chem. 2016; 1156
• 59 Riché F, Masri F, Lopez M. Tetrahedron Lett. 2007; 48: 1609
• 60 Davies HM. L, Saikali E, Huby NJ. S, Gilliatt VJ, Matasi JJ, Sexton T, Childers SR. J. Med. Chem. 1994; 37: 1262
• 61 Reddy RP, Davies HM. L. J. Am. Chem. Soc. 2007; 129: 10312
• 62 Parr BT, Economou C, Herzon SB. Nature (London) 2015; 525: 507
• 63 Economou C, Romaire JP, Scott TZ, Parr BT, Herzon SB. Tetrahedron 2018; 74: 3188
• 64 Kende AS, Smalley TL, Huang H. J. Am. Chem. Soc. 1999; 121: 7431
• 65 Davies HM. L, Matasi JJ. Tetrahedron Lett. 1994; 35: 5209
• 66 Davies HM. L, Matasi JJ, Ahmed G. J. Org. Chem. 1996; 61: 2305
• 67 Jeffrey CS, Barnes KL, Eickhoff JA, Carson CR. J. Am. Chem. Soc. 2011; 133: 7688
• 68 Acharya A, Eickhoff JA, Jeffrey CS. Synthesis 2013; 45: 1825
• 69a Lo B, Lam S, Wong WT, Chiu P. Angew. Chem. Int. Ed. 2012; 51: 12120
• 69b Krenske EH, Lam S, Ng JP. L, Lo B, Lam SK, Chiu P, Houk KN. Angew. Chem. Int. Ed. 2015; 54: 7422
• 70 He J, Chen Z, Li W, Low K.-H, Chiu P. Angew. Chem. Int. Ed. 2018; 57: 5253
• 71 Okamoto T, Shibata M, Karanjit S, Nakayama A, Yoshida M, Namba K. Chem. Eur. J. 2018; 24: 9508