Synlett 2014; 25(4): 466-476
DOI: 10.1055/s-0033-1340472
account
© Georg Thieme Verlag Stuttgart · New York

Adventures in Ring-Contraction Reactions

Luiz F. Silva Jr.*
Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes 748, CP 26077, CEP 05513-970 São Paulo SP, Brazil   Fax: +55(128)155579   Email: luizfsjr@iq.usp.br
› Author Affiliations
Further Information

Publication History

Received: 28 October 2013

Accepted after revision: 21 November 2013

Publication Date:
13 January 2014 (online)


Dedicated to Joaquim L. Matheus for 20 years of tremendous help in the lab.

Abstract

Nearly two decades of work on ring-contraction reactions is discussed in this account. We have developed several reliable protocols for the rearrangement of a number of different substrates using thallium(III) salts and, more recently, hypervalent iodine(III) reagents. A variety of ring systems, such as cyclopentanes, cis- and trans-hydrindanes, and indanes, can be obtained using these methods. Additionally, the stereoselective total syntheses of the sesquiterpenes (±)-, (–)- and (+)-mutisianthol and (+)-bakkenolide A, the indole alkaloid (±)- and (+)-trans-trikentrin A, and the potential drug (±)-indatraline have been achieved through a ring-contraction approach.

1 Introduction

2 Ring-Contraction Reactions Promoted by Thallium(III)

2.1 Thallium(III)-Mediated Ring Contraction of Cyclic Ketones

2.2 Thallium(III)-Mediated Ring Contraction of Cyclic Olefins

2.3 Thallium(III)-Mediated Ring Contraction of Homoallylic Alcohols

3 Ring-Contraction Reactions Promoted by Iodine(III)

4 Conclusion

 
  • References

  • 1 Nicolaou KC. J. Org. Chem. 2009; 74: 951
  • 2 Kumar K, Waldmann H. Angew. Chem. Int. Ed. 2009; 48: 3224
  • 3 Wender PA, Miller BL. Nature 2009; 460: 197
  • 4 Ley SV. Tetrahedron 2010; 66: 6270
  • 5 Gaich T, Baran PS. J. Org. Chem. 2010; 75: 4657
  • 6 Schreiber SL. Proc. Natl. Acad. Sci. U.S.A. 2011; 108: 6699
  • 7 Huigens RW, Morrison KC, Hicklin RW, Flood TA, Richter MF, Hergenrother PJ. Nature Chem. 2013; 5: 195
  • 8 Silva LF. Jr. Tetrahedron 2002; 58: 9137
  • 9 Belov VN, Wurm CA, Boyarskiy VP, Jakobs S, Hell SW. Angew. Chem. Int. Ed. 2010; 49: 3520
  • 10 Bigi MA, Reed SA, White MC. Nature Chem. 2011; 3: 216
  • 11 Kita Y, Higuchi K, Yoshida Y, Iio K, Kitagaki S, Ueda K, Akai S, Fujioka H. J. Am. Chem. Soc. 2001; 123: 3214
  • 12 Snyder SA, Corey EJ. J. Am. Chem. Soc. 2006; 128: 740
  • 13 Mascitti V, Corey EJ. J. Am. Chem. Soc. 2006; 128: 3118
  • 14 Takasu K, Nagamoto Y, Takemoto Y. Chem. Eur. J. 2010; 16: 8427
  • 15 Redmore D, Gutsche CD In Advances in Alicyclic Chemistry . Vol. 3. Hart H, Karabastos GJ. Academic; New York: 1971: 1
  • 16 McKillop A, Taylor EC In Comprehensive Organometallic Chemistry . Vol. 7. Wilkinson G. Pergamon; New York: 1982: 465
  • 17 McKillop A, Taylor EC In Organic Syntheses by Oxidation with Metal Compounds . Miss WJ, De Jonge CR. H. I. Plenum; New York: 1986: 695
  • 18 Ferraz HM. C, Silva LF. Jr, Vieira TO. Synthesis 1999; 2001
  • 19 Silva LF. Jr, Carneiro VM. T. Synthesis 2010; 1059
  • 20 Silva LF. Jr. Molecules 2006; 11: 421
  • 21 Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299
  • 22 Silva LF. Jr, Olofsson B. Nat. Prod. Rep. 2011; 28: 1722
  • 23 Singh FV, Wirth T. Synthesis 2013; 45: 2499
  • 24 Varvoglis A. Hypervalent Iodine in Organic Synthesis . Academic; San Diego: 1997
  • 25 Wirth T In Hypervalent Iodine Chemistry: Modern Developments in Organic Synthesis. Vol. 224. Springer; Heidelberg: 2003: 1
  • 26 Ferraz HM. C, Silva LF. Jr. Tetrahedron Lett. 1997; 38: 1899
  • 27 McKillop A, Hunt JD, Taylor EC. J. Org. Chem. 1972; 37: 3381
  • 28 Wiberg KB, Koch W. Tetrahedron Lett. 1966; 1779
  • 29 Farcasiu D, Schleyer PV. R, Ledlie DB. J. Org. Chem. 1973; 38: 3455
  • 30 South AJr, Ouellette RJ. J. Am. Chem. Soc. 1968; 90: 7064
  • 31 Ouellette RJ, Kordosky G, Levin C, Williams S. J. Org. Chem. 1969; 34: 4104
  • 32 Gavande N, Yamamoto I, Salam NK, Ai TH, Burden PM, Johnston GA. R, Hanrahan JR, Chebib M. ACS Med. Chem. Lett. 2011; 2: 11
  • 33 Mitcheltree MJ, Konst ZA, Herzon SB. Tetrahedron 2013; 69: 5634
  • 34 Moriarty RM, Enache LA, Zhao L, Gilardi R, Mattson MV, Prakash O. J. Med. Chem. 1998; 41: 468
  • 35 Ferraz HM. C, Silva LF. Jr. J. Org. Chem. 1998; 63: 1716
  • 36 Norden S, Bender M, Rullkötter J, Christoffers J. Eur. J. Org. Chem. 2011; 4543
  • 37 Sanchez-Flores J, Pelayo-Gonzalez VG, Romero-Avila M, Flores-Perez B, Flores-Alamo M, Iglesias-Arteaga MA. Steroids 2013; 78: 234
  • 38 Ferraz HM. C, Silva LF. Jr. J. Braz. Chem. Soc. 2001; 12: 548
  • 39 Silva LF. Jr. Synthesis 2001; 671
  • 40 Buchschacher P, Fürst A, Gutzwiller J. Org. Synth. 1985; 63: 37
  • 41 Carneiro VM. T, Ferraz HM. C, Vieira TO, Ishikawa EE, Silva LF. Jr. J. Org. Chem. 2010; 75: 2877
  • 42 Ferraz HM. C, Silva LF. Jr, Aguilar AM, Vieira TO. J. Braz. Chem. Soc. 2001; 12: 680
  • 43 Taylor EC, Chiang C.-S, McKillop A, White JF. J. Am. Chem. Soc. 1976; 98: 6750
  • 44 Singh OV, Muthukrishman M, Sundaravedivelu M. Synth. Commun. 2006; 36: 943
  • 45 Justik MW. Tetrahedron Lett. 2007; 48: 3003
  • 46 Ferraz HM. C, Silva LF. Jr. Quim. Nova 2000; 23: 216
  • 47 Kabbe H.-J. Justus Liebigs Ann. Chem. 1962; 656: 204
  • 48 McKillop A, Hunt JD, Kienzle F, Bigham E, Taylor EC. J. Am. Chem. Soc. 1973; 95: 3635
  • 49 Ferraz HM. C, Silva LF. Jr, Vieira TO. Tetrahedron 2001; 57: 1709
  • 50 Ferraz HM. C, Aguilar AM, Silva LF. Jr. Synthesis 2003; 7: 1031
  • 51 Silva LF. Jr, Sousa RM. F, Ferraz HM. C, Aguilar AM. J. Braz. Chem. Soc. 2005; 16: 1160
  • 52 Ferraz HM. C, Carneiro VM. T, Silva LF. Jr. Synthesis 2009; 385
  • 53 Ferraz HM. C, Aguilar AM, Silva LF. Jr. Tetrahedron 2003; 59: 5817
  • 54 Bianco GG, Ferraz HM. C, Costa AM, Costa-Lotufo LV, Pessoa C, de Moraes MO, Schrems MG, Pfaltz A, Silva LF. Jr. J. Org. Chem. 2009; 74: 2561
  • 55 Fananas FJ, Alvarez-Perez M, Rodriguez F. Chem. Eur. J. 2005; 11: 5938
  • 56 Silva LF. Jr, Craveiro MV, Gambardella MT. P. Synthesis 2007; 3851
  • 57 Silva LF. Jr, Craveiro MV. Org. Lett. 2008; 10: 5417
  • 58 Tébéka IR. M, Longato GB, Craveiro MV, de Carvalho JE, Ruiz AL. T. G, Silva LF. Jr. Chem. Eur. J. 2012; 18: 16890
  • 59 Arp FO, Fu GC. J. Am. Chem. Soc. 2005; 127: 10482
  • 60 Macleod JK, Monahan LC. Aust. J. Chem. 1990; 43: 329
  • 61 Muratake H, Watanabe M, Goto K, Natsume M. Tetrahedron 1990; 46: 4179
  • 62 Boger DL, Zhang M. J. Am. Chem. Soc. 1991; 113: 4230
  • 63 Silva LF. Jr, Craveiro MV, Tébéka IR. M. Tetrahedron 2010; 66: 3875
  • 64 Ferraz HM. C, Vieira TO, Silva LF. Jr. Synthesis 2006; 2748
  • 65 Ferraz HM. C, Carneiro VM. T, Vieira TO, Silva LF. Jr. Quim. Nova 2008; 31: 781
  • 66 Ferraz HM. C, Silva LF. Jr. Tetrahedron 2001; 57: 9939
  • 67 Silva LF. Jr, Quintiliano SA. P, Craveiro MV, Vieira FY. M, Ferraz HM. C. Synthesis 2007; 355
  • 68 Paddon-Row MN, Rondan NG, Houk KN. J. Am. Chem. Soc. 1982; 104: 7162
  • 69 Ferraz HM. C, Santos AP, Silva LF. Jr, Vieira Tde O. Synth. Commun. 2000; 30: 751
  • 70 Silva LF. Jr, Quintiliano SA. P, Ferraz HM. C, Santos LS, Eberlin MN. J. Braz. Chem. Soc. 2006; 17: 981
  • 71 Ferraz HM. C, Longo LS. Jr, Zukerman-Schpector J. J. Org. Chem. 2002; 67: 3518
  • 72 Preite MD, Cuellar MA. Chem. Commun. (Cambridge) 2004; 1970
  • 73 Kocovský P, Baines RS. Tetrahedron Lett. 1993; 34: 6139
  • 74 Kocovský P, Baines RS. J. Org. Chem. 1994; 59: 5439
  • 75 Ferraz HM. C, Silva LF. Jr. Synthesis 2002; 1033
  • 76 Silva LF. Jr, Craveiro MV. Molecules 2005; 10: 1419
  • 77 Galván-Arzate S, Santamaria A. Toxicol. Lett. 1998; 99: 1
  • 78 Léonard A, Gerber GB. Mutat. Res. 1997; 387: 47
  • 79 Koser GF. Aldrichimica Acta 2001; 34: 89
  • 80 Justik MW, Koser GF. Tetrahedron Lett. 2004; 45: 6159
  • 81 Silva LF. Jr, Siqueira FA, Pedrozo EC, Vieira FY. M, Doriguetto AC. Org. Lett. 2007; 9: 1433
  • 82 Siqueira FA, Ishikawa EE, Fogaça A, Faccio AT, Carneiro VM. T, Soares RR. S, Utaka A, Tébeká IR. M, Bielawski M, Olofsson B, Silva LF. Jr. J. Braz. Chem. Soc. 2011; 22: 1795
  • 83 Kameyama M, Siqueira FA, Garcia-Mijares M, Silva LF. Jr, Silva MT. A. Molecules 2011; 16: 9421
  • 84 Bogeso KP, Christensen AV, Hyttel J, Liljefors T. J. Med. Chem. 1985; 28: 1817
  • 85 Mello NK, Negus SS. Neuropsychopharmacology 2001; 25: 104
  • 86 Hawkins JM, Watson TJ. N. Angew. Chem. Int. Ed. 2004; 43: 3224
  • 87 Lucero MJ, Houk KN. J. Org. Chem. 1998; 63: 6973
  • 88 Martinelli MJ, Peterson BC, Khau VV, Hutchison DR, Leanna MR, Audia JE, Droste JJ, Wu YD, Houk KN. J. Org. Chem. 1994; 59: 2204
  • 89 Maeda K, Brown JM. Chem. Commun. (Cambridge) 2002; 310
  • 90 Dohi T, Yamaoka N, Kita Y. Tetrahedron 2010; 66: 5775
  • 91 Farid U, Malmedy F, Claveau R, Albers L, Wirth T. Angew. Chem. Int. Ed. 2013; 52: 7018
  • 92 Ahmad A, Silva LF. Jr. Synthesis 2012; 44: 3671
  • 93 Merritt EA, Carneiro VM. T, Silva LF. Jr, Olofsson B. J. Org. Chem. 2010; 75: 7416
  • 94 Ahmad A, Scarassati P, Jalalian N, Olofsson B, Silva LF. Tetrahedron Lett. 2013; 54: 5818