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Synthesis 2014; 46(19): 2629-2643
DOI: 10.1055/s-0034-1378356
DOI: 10.1055/s-0034-1378356
paper
Palladium-Catalyzed Ring Opening of Cyclopropane-Appended Spirotricyclic Olefins with Soft Nucleophiles and Organoboronic Acids: Facile Synthesis of Functionalized Spiro[2.4]heptenes
Further Information
Publication History
Received: 21 April 2014
Accepted after revision: 02 June 2014
Publication Date:
14 July 2014 (online)
Abstract
The palladium-catalyzed ring opening of cyclopropane- and vinylcyclopropane-appended spirotricyclic olefins by employing active methylene compounds, phenols and organoboronic acids is discussed in detail. The present strategy provides a facile route for the synthesis of biologically significant, functionalized spiro[2.4]heptenes under mild reaction conditions. The synthetic utility of the described compounds is emphasized by the preparation of the corresponding iodolactone derivatives and a highly substituted spiro[2.4]heptane.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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References
- 1a Bournaud C, Chung F, Luna AP, Pasco M, Errasti G, Lecourt T, Micouin L. Synthesis 2009; 869
- 1b Sajisha VS, Anas S, John J, Radhakrishnan KV. Synlett 2009; 2885
-
2a Lillelund VH, Jensen HH, Liang X, Bols M. Chem. Rev. 2002; 102: 515
-
2b Trost BM, Van Vranken DL. J. Am. Chem. Soc. 1993; 115: 444
- 2c Ogawa S, Morikawa T. Eur. J. Org. Chem. 2000; 1759
- 2d Puder C, Krastel P, Zeeck A. J. Nat. Prod. 2000; 63: 1258
- 2e Revial G, Jahin I, Pfau M. Tetrahedron: Asymmetry 2000; 11: 4975
- 3a Crotti S, Bertolini F, Macchia F, Pineschi M. Adv. Synth. Catal. 2009; 351: 869
- 3b Crotti S, Bertolini F, Macchia F, Pineschi M. Chem. Commun. 2008; 312
- 3c Pineschi M, Moro FD, Crotti P, Macchia F. Org. Lett. 2005; 7: 3605
-
4a Bexrud J, Lautens M. Org. Lett. 2010; 12: 3160
- 4b Martins A, Lemouzy S, Lautens M. Org. Lett. 2009; 11: 181
- 4c Menard F, Lautens M. Angew. Chem. Int. Ed. 2008; 47: 2085
- 4d Menard F, Weise CF, Lautens M. Org. Lett. 2007; 9: 5365
- 5a Storsberg J, Nandakumar MV, Sankaranarayanan S, Kaufmann DE. Adv. Synth. Catal. 2001; 343: 177
- 5b Yao ML, Adiwidjaja G, Kaufmann DE. Angew. Chem. Int. Ed. 2002; 41: 3375
- 6a Palais L, Bournaud C, Micouin L, Alexakis A. Chem. Eur. J. 2010; 16: 2567
- 6b Palais L, Mikhel IS, Bournaud C, Micouin L, Falciola CA, Vuagnoux-d’Augustin M, Rosset S, Bernardinelli G, Alexakis A. Angew. Chem. Int. Ed. 2007; 46: 7462
- 6c Bournaud C, Bonin M, Micouin L. Org. Lett. 2006; 8: 3041
- 6d Bournaud C, Falciola C, Lecourt T, Rosset S, Alexakis A, Micouin L. Org. Lett. 2006; 8: 3581
- 6e Luna AP, Cesario M, Bonin M, Micouin L. Org. Lett. 2003; 5: 4771
- 6f Bournaud C, Lecourt T, Micouin L, Méliet C, Agbossou-Niedercorn F. Eur. J. Org. Chem. 2008; 2298
- 6g Luna AP, Bonin M, Micouin L, Husson H.-P. J. Am. Chem. Soc. 2002; 124: 12098
- 7a Radhakrishnan KV, Sajisha VS, Anas S, Krishnan KS. Synlett 2005; 2273
- 7b Sajisha VS, Mohanlal S, Anas S, Radhakrishnan KV. Tetrahedron 2006; 62: 3997
- 7c Sajisha VS, Radhakrishnan KV. Adv. Synth. Catal. 2006; 348: 924
- 7d John J, Anas S, Sajisha VS, Viji S, Radhakrishnan KV. Tetrahedron Lett. 2007; 48: 7225
- 7e Anas S, Sajisha VS, John J, Joseph N, George SC, Radhakrishnan KV. Tetrahedron 2008; 64: 9689
- 7f John J, Adarsh B, Radhakrishnan KV. Tetrahedron 2010; 66: 1383
- 7g John J, Sajisha VS, Mohanlal S, Radhakrishnan KV. Chem. Commun. 2006; 3510
- 7h Anas S, John J, Sajisha VS, John J, Rajan R, Suresh E, Radhakrishnan KV. Org. Biomol. Chem. 2007; 5: 4010
- 7i Rajan R, John J, Thulasi S, Joseph N, Radhakrishnan KV, Sawant RC. Synthesis 2010; 3649
- 8 Bhanu Prasad BA, Buechele AE, Gilbertson SR. Org. Lett. 2010; 12: 5422
- 9a John J, Indu U, Suresh E, Radhakrishnan KV. J. Am. Chem. Soc. 2009; 131: 5042
- 9b Jijy E, Prakash P, Shimi M, Pihko PM, Joseph N, Radhakrishnan KV. Chem. Commun. 2013; 49: 7349
- 9c Sarath Chand S, Jijy E, Prakash P, Szymoniak J, Preethanuj P, Dhanya BP, Radhakrishnan KV. Org. Lett. 2013; 15: 3338
- 9d Jijy E, Prakash P, Saranya S, Suresh E, Radhakrishnan KV. Synthesis 2013; 45: 2583
- 9e Joseph N, John J, Rajan R, Thulasi S, Mohan A, Suresh E, Radhakrishnan KV. Tetrahedron 2011; 67: 4905
- 10a Prakash P, Jijy E, Preethanuj P, Pihko PM, Sarath Chand S, Radhakrishnan KV. Chem. Eur. J. 2013; 19: 10473
- 10b Prakash P, Jijy E, Shimi M, Aparna PS, Suresh E, Radhakrishnan KV. RSC Adv. 2013; 3: 19933
- 11a Wessjohann LA, Brandt W, Thiemann T. Chem. Rev. 2003; 103: 1625
- 11b Baldwin JE, Parker DW. Chem. Rev. 2003; 103: 1197
- 11c Salaun J. Cyclopropane Derivatives and Their Diverse Biological Activities. In Small Ring Compounds in Organic Synthesis VI. de Meijere A. Springer-Verlag; Berlin: 1999: 240
- 11d Cao W, Zhang H, Chen J, Deng H, Shao M, Lei L, Qian J, Zhu Y. Tetrahedron 2008; 64: 6670
- 11e Salaun J. Top. Curr. Chem. 2000; 207: 1
- 12a Kim SY, Park HB, Cho J.-H, Yoo KH, Oh CH. Bioorg. Med. Chem. Lett. 2009; 19: 2558
- 12b Liu LJ, Kim E, Hong JH. Nucleosides, Nucleotides Nucleic Acids 2011; 30: 784
- 12c Tymtsunik AV, Bilenko VA, Ivon YM, Grygorenko OO, Komarov IV. Tetrahedron Lett. 2012; 53: 3847
- 12d Reitz DB, Huang H.-C, Li JJ, Garland DJ, Manning RE. Bioorg. Med. Chem. Lett. 1995; 5: 867
- 12e Chesterfield DB. R, StLouis RE. M, Huang H.-C, Li J. International Patent PCT/US1995/5393790, 1995
- 12f Kostyuchenko IV, Shulishov EV, Korolev VA, Dokichev VA, Tomilov YV. Russ. Chem. Bull. 2005; 54: 2562
- 12g Curry K. International Patent PCT/US2004/0077599, 2004
- 13 The crystal data for compound 9d have been deposited with the Cambridge Crystallographic Data Centre (no. CCDC 965586). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk] or via www.ccdc.cam.ac.uk/data_request/cif.