RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2014; 46(10): 1279-1296
DOI: 10.1055/s-0033-1341073
DOI: 10.1055/s-0033-1341073
review
High-Pressure Transformations in Natural Product Synthesis
Weitere Informationen
Publikationsverlauf
Received: 21. November 2013
Accepted after revision: 12. Dezember 2013
Publikationsdatum:
07. April 2014 (online)
Abstract
This review summarizes the application of high-pressure chemistry in natural product synthesis. By highlighting reactions that could not be promoted by conventional means but that proceed readily under high-pressure conditions, we intend to disclose the benefits of high-pressure-mediated reactions for organic transformations. The individual syntheses are classified by the reaction type of the key step and are discussed briefly.
1 Introduction
2 Cycloaddition Reactions
2.1 Diels–Alder Reactions
2.2 Inverse-Electron-Demand Diels–Alder Reactions
2.3 Hetero-Diels–Alder Reactions
3 Miscellaneous Reactions
4 Conclusion
-
References
- 1 Jenner G. The Future of High Pressure Organic Synthesis. Vol. 401. Springer; Amsterdam: 1993
- 2a Industrial High Pressure Applications, Processes, Equipment and Safety. 1st ed.; Eggers R. Wiley-VCH; Weinheim: 2012
- 2b High Pressure Chemistry. van Eldik R, Klärner FG. Wiley-VCH; Weinheim: 2008
- 3a Matsumoto K, Hamana H, Iida H. Helv. Chim. Acta 2005; 88: 2033
- 3b Matsumoto K. High-Pressure Synthesis of Heterocycles Related to Bioactive Molecules. Springer; Berlin/Heidelberg: 2007
- 5a Jenner G. Tetrahedron 1997; 53: 2669
- 5b Tietze LF, Henrich M, Niklaus A, Buback M. Chem. Eur. J. 1999; 5: 297
- 6 Jenner G. Tetrahedron 2002; 58: 5185
- 7 van Berkom LW, Kuster GJ, Scheeren HW. Mol. Diversity 2003; 6: 271
- 8a Ciobanu M, Matsumoto K. Liebigs Ann. Chem. Rec. 1997; 623
- 8b Kotsuki H, Kumamoto K. J. Synth. Org. Chem Jpn. 2005; 63: 770
- 8c Benito-Lopez F, Egberink RJ, Reinhoudt DN, Verboom W. Tetrahedron 2008; 64: 10023
- 9a Dauben WG, Kozikowski AP. J. Am. Chem. Soc. 1974; 96: 3664
- 9b Dauben WG, Krabbenhoft HO. J. Am. Chem. Soc. 1976; 98: 1992
- 9c Dauben WG, Krabbenhoft HO. J. Org. Chem. 1977; 42: 282
- 10 Karras DJ, Farrell SE, Harrigan RA, Henretig FM, Gealt L. Am. J. Emerg. Med. 1996; 14: 478
- 11a Dauben WG, Gerdes JM, Smith DB. J. Org. Chem. 1985; 50: 2576
- 11b Dauben WG, Kessel CR, Takemura KH. J. Am. Chem. Soc. 1980; 102: 6893
- 12 Stork G, Nakamura E. J. Am. Chem. Soc. 1983; 105: 5510
- 13 Speck K, Magauer T. Beilstein J. Org. Chem. 2013; 9: 2048
- 14 Wadsworth W, Emmons WD. J. Am. Chem. Soc. 1961; 83: 1733
- 15 Smith AB, Liverton NJ, Hrib NJ, Sivaramakrishnan H, Winzenberg K. J. Am. Chem. Soc. 1986; 108: 3040
- 16 Taylor MD, Minaskanian G, Winzenberg KN, Santone P, Smith AB. J. Org. Chem. 1982; 47: 3960
- 17 Mukaiyama T, Banno K, Narasaka K. J. Am. Chem. Soc. 1974; 96: 7503
- 18 Hirsenkorn R, Haagzeino B, Schmidt RR. Tetrahedron Lett. 1990; 31: 4433
- 19 Ireland RE, Mueller RH. J. Am. Chem. Soc. 1972; 94: 5897
- 20 Hirsenkorn R, Schmidt RR. Liebigs Ann. Chem. 1990; 883
- 21 Nakagawa M. J. Heterocycl. Chem. 2000; 37: 567
- 22a Torisawa Y, Nakagawa M, Arai H, Lai Z, Hino T, Nakata T, Oishi T. Tetrahedron Lett. 1990; 31: 3195
- 22b Torisawa Y, Nakagawa M, Hosaka T, Tanabe K, Lai ZP, Ogata K, Nakata T, Oishi T, Hino T. J. Org. Chem. 1992; 57: 5741
- 23 Waalboer CJ. D, Schaapman MC, van Delft FL, Rutjes FP. J. T. Angew. Chem. Int. Ed. 2008; 47: 6576
- 24a Nicolaou KC, Tria GS, Edmonds DJ. Angew. Chem. Int. Ed. 2008; 47: 1780
- 24b Hayashida J, Rawal VH. Angew. Chem. Int. Ed. 2008; 47: 4373
- 25 Danishefsky S, Kitahara T, Yan CF, Morris J. J. Am. Chem. Soc. 1979; 101: 6996
- 27 Danishefsky S, Kerwin JF. J. Org. Chem. 1982; 47: 3183
- 28 Engler TA, Sampath U, Naganathan S, Velde DV, Takusagawa F, Yohannes D. J. Org. Chem. 1989; 54: 5712
- 29 Matsumoto T, Tachiban Y, Uchida J, Fukui K. Bull. Chem. Soc. Jpn. 1971; 44: 2766
- 30a Harwood LM, Jones G, Pickard J, Thomas RM, Watkin D. J. Chem. Soc., Chem. Commun. 1990; 605
- 30b Harwood LM, Jackson B, Jones G, Prout K, Thomas RM, Witt FJ. J. Chem. Soc., Chem. Commun. 1990; 608
- 30c Harwood LM, Ishikawa T, Phillips H, Watkin D. J. Chem. Soc., Chem. Commun. 1991; 527
- 31 Brickwood AC, Drew MG. B, Harwood LM, Ishikawa T, Marais P, Morisson V. J. Chem. Soc., Perkin Trans. 1 1999; 913
- 32 Marrero JG, Harwood LM. Tetrahedron Lett. 2009; 50: 3574
- 33 Inoue M, Takenaka H, Tsurushima T, Miyagawa H, Ueno T. Tetrahedron Lett. 1996; 37: 8823
- 34 Drew MG. B, Jahans A, Harwood LM, Apoux SA. B. H. Eur. J. Org. Chem. 2002; 3589
- 35a Minuti L, Temperini A, Ballerini E. J. Org. Chem. 2012; 77: 7923
- 35b Ballerini E, Minuti L, Piermatti O. J. Org. Chem. 2010; 75: 4251
- 35c Minuti L, Ballerini E. J. Org. Chem. 2011; 76: 5392
- 35d Ballerini E, Minuti L, Piermatti O, Pizzo F. J. Org. Chem. 2009; 74: 4311
- 36a Pandey SK, Orellana A, Greene AE, Poisson JF. Org. Lett. 2006; 8: 5665
- 36b Orellana A, Pandey SK, Carret S, Greene AE, Poisson JF. J. Org. Chem. 2012; 77: 5286
- 37 Pasfield LA, Cruz L, Ho J, Coote ML, Otting G, McLeod MD. Asian J. Org. Chem. 2013; 2: 60
- 38a Banwell MG, Edwards AJ, Harfoot GJ, Jolliffe KA. J. Chem. Soc., Perkin Trans. 1 2002; 2439
- 38b Banwell MG, Edwards AJ, Harfoot GJ, Jolliffe KA. Tetrahedron 2004; 60: 535
- 39 Hudlicky T, Gonzalez D, Gibson DT. Aldrichimica Acta 1999; 32
- 40 Banwell MG, Bridges VS, Dupuche JR, Richards SL, Walter JM. J. Org. Chem. 1994; 59: 6338
- 41 Zimmerman HE, Armesto D. Chem. Rev. 1996; 96: 3065
- 42 Banwell MG, Austin KA. B, Willis AC. Tetrahedron 2007; 63: 6388
- 43 Matzanke N, Gregg RJ, Weinreb SM, Parvez M. J. Org. Chem. 1997; 62: 1920
- 44 Achmatow O, Bukowski P, Szechner B, Zwierzch Z, Zamojski A. Tetrahedron 1971; 27: 1973
- 45 Murahashi S, Makabe Y, Kunita K. J. Org. Chem. 1988; 53: 4489
- 46 Hatsui T, Hashiguchi T, Takeshita H. Chem. Lett. 1994; 1415
- 47 Kienzler MA, Suseno S, Trauner D. J. Am. Chem. Soc. 2008; 130: 8604
- 48 Wipf P, Halter RJ. Org. Biomol. Chem. 2005; 3: 2053
- 49 Hughes CC, Kennedy-Smith JJ, Trauner D. Org. Lett. 2003; 5: 4113
- 50 Dounay AB, Overman LE. Chem. Rev. 2003; 103: 2945
- 51 Liu L, Liu SC, Jiang LH, Chen XL, Guo LD, Che YS. Org. Lett. 2008; 10: 1397
- 52 Suzuki T, Kobayashi S. Org. Lett. 2010; 12: 2920
- 53 Suzuki T, Miyajima Y, Suzuki K, Iwakiri K, Koshimizu M, Hirai G, Sodeoka M, Kobayashi S. Org. Lett. 2013; 15: 1748
- 54a Jurczak J, Chmielewski M, Filipek S. Synthesis 1979; 41
- 54b Chmielewski M, Jurczak J. J. Org. Chem. 1981; 46: 2230
- 54c Jurczak J, Tkacz M. J. Org. Chem. 1979; 44: 3347
- 55 Daniewski WM, Kubak E, Jurczak J. J. Org. Chem. 1985; 50: 3963
- 56 Kobayashi J, Cheng JF, Nakamura H, Ohizumi Y, Hirata Y, Sasaki T, Ohta T, Nozoe S. Tetrahedron Lett. 1988; 29: 1177
- 57 Alvarez M, Feliu L, Ajana W, Joule JA, Fernandez-Puentes JL. Eur. J. Org. Chem. 2000; 849
- 58 Golebiowski A, Jacobsson U, Jurczak J. Tetrahedron 1987; 43: 3063
- 59 Jurczak J, Golebiowski A, Bauer T. Synthesis 1985; 928
- 60 Golebiowski A, Jacobsson U, Chmielewski M, Jurczak J. Tetrahedron 1987; 43: 599
- 61 Wright J, Drtina GJ, Roberts RA, Paquette LA. J. Am. Chem. Soc. 1988; 110: 5806
- 62 Still WC, Mitra A. J. Am. Chem. Soc. 1978; 100: 1927
- 63 Bal BS, Childers WE, Pinnick HW. Tetrahedron 1981; 37: 2091
- 64 Han G, LaPorte MG, Folmer JJ, Werner KM, Weinreb SM. Angew. Chem. Int. Ed. 2000; 39: 237
- 65 Han G, LaPorte MG, McIntosh MC, Weinreb SM, Parvez M. J. Org. Chem. 1996; 61: 9483
- 66 Heathcock CH, Mahaim C, Schlecht MF, Utawanit T. J. Org. Chem. 1984; 49: 3264
- 67 Matsumoto K. Angew. Chem., Int. Ed. Engl. 1980; 19: 1013
- 68 Bunce RA, Schlecht MF, Dauben WG, Heathcock CH. Tetrahedron Lett. 1983; 24: 4943
- 69 Kerwin SM, Paul AG, Heathcock CH. J. Org. Chem. 1987; 52: 1686
- 70 Kinoshita Y, Kitahara T. Tetrahedron Lett. 1997; 38: 4993
- 71 Shimizu T, Masuda T, Hiramoto K, Nakata T. Org. Lett. 2000; 2: 2153
- 72 El Sous M, Ganame D, Tregloan PA, Rizzacasa MA. Org. Lett. 2004; 6: 3001
- 73 Smith AB, Kaufman MD, Beauchamp TJ, LaMarche MJ, Arimoto H. Org. Lett. 1999; 1: 1823
- 74 Appel R. Angew. Chem., Int. Ed. Engl. 1975; 14: 801
- 75a Mickel SJ, Sedelmeier GH, Niederer D, Daeffler R, Osmani A, Schreiner K, Seeger-Weibel M, Bérod B, Schaer K, Gamboni R, Chen S, Chen W, Jagoe CT, Kinder FR, Loo M, Prasad K, Repič O, Shieh W.-C, Wang R.-M, Waykole L, Xu DD, Xue S. Org. Process Res. Dev. 2003; 8: 92
- 75b Mickel SJ, Sedelmeier GH, Niederer D, Schuerch F, Grimler D, Koch G, Daeffler R, Osmani A, Hirni A, Schaer K, Gamboni R, Bach A, Chaudhary A, Chen S, Chen W, Hu B, Jagoe CT, Kim H.-Y, Kinder FR, Liu Y, Lu Y, McKenna J, Prashad M, Ramsey TM, Repič O, Rogers L, Shieh W.-C, Wang R.-M, Waykole L. Org. Process Res. Dev. 2003; 8: 101
- 75c Mickel SJ, Sedelmeier GH, Niederer D, Schuerch F, Koch G, Kuesters E, Daeffler R, Osmani A, Seeger-Weibel M, Schmid E, Hirni A, Schaer K, Gamboni R, Bach A, Chen S, Chen W, Geng P, Jagoe CT, Kinder FR, Lee GT, McKenna J, Ramsey TM, Repič O, Rogers L, Shieh W.-C, Wang R.-M, Waykole L. Org. Process Res. Dev. 2003; 8: 107
- 75d Mickel SJ, Sedelmeier GH, Niederer D, Schuerch F, Seger M, Schreiner K, Daeffler R, Osmani A, Bixel D, Loiseleur O, Cercus J, Stettler H, Schaer K, Gamboni R, Bach A, Chen G.-P, Chen W, Geng P, Lee GT, Loeser E, McKenna J, Kinder FR, Konigsberger K, Prasad K, Ramsey TM, Reel N, Repič O, Rogers L, Shieh W.-C, Wang R.-M, Waykole L, Xue S, Florence G, Paterson I. Org. Process Res. Dev. 2003; 8: 113
- 75e Mickel SJ, Niederer D, Daeffler R, Osmani A, Kuesters E, Schmid E, Schaer K, Gamboni R, Chen W, Loeser E, Kinder FR, Konigsberger K, Prasad K, Ramsey TM, Repič O, Wang R.-M, Florence G, Lyothier I, Paterson I. Org. Process Res. Dev. 2003; 8: 122
- 76 Kotsuki H, Teraguchi M, Shimomoto N, Ochi M. Tetrahedron Lett. 1996; 37: 3727