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 2016; 48(09): 1399-1406
DOI: 10.1055/s-0035-1561366
DOI: 10.1055/s-0035-1561366
paper
Microwave-Promoted Deprenylation: Prenyl Ether as a Thermolabile Phenol Protecting Group
Weitere Informationen
Publikationsverlauf
Received: 28. Oktober 2015
Accepted after revision: 14. Januar 2016
Publikationsdatum:
10. Februar 2016 (online)
Abstract
para-Substituted aryl prenyl ethers undergo a deprenylation reaction upon microwave irradiation. This offers the opportunity to use a prenyl ether as a thermolabile protecting group in the synthesis of natural products with a chromone structure, which proceeds via a tandem deprenylation/6-endo-cyclization sequence.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561366.
- Supporting Information
-
References
- 1 Kocieński PJ. Protecting Groups . Georg Thieme Verlag; Stuttgart: 2003
- 2 Guibé F. Tetrahedron 1997; 53: 13509
- 3 Guibé F. Tetrahedron 1998; 54: 2967
- 4 Bartoli G, Cupone G, Dalpozzo R, De Nino A, Maiuolo L, Marcantoni E, Procopio A. Synlett 2001; 1897
- 5 Thomas RM, Reddy GS, Iyengar DS. Tetrahedron Lett. 1999; 40: 7293
- 6 Gärtner D, Konnerth H, von Wangelin AJ. Catal. Sci. Technol. 2013; 3: 2541
- 7 Gigg R. J. Chem. Soc., Perkin Trans. 1 1980; 738
- 8 Yadav JS, Subba Reddy BV. Carbohydr. Res. 2000; 329: 885
- 9 Sharma GV. M, Ilangovan A, Mahalingam AK. J. Org. Chem. 1998; 63: 9103
- 10 Tsuritani T, Shinokubo H, Oshima K. Tetrahedron Lett. 1999; 40: 8121
- 11 Sharma GV. M, Reddy CG, Krishna PR. Synlett 2003; 1728
- 12 Suresh Babu K, China Raju B, Srinivas PV, Madhusudana Rao J. Tetrahedron Lett. 2003; 44: 2525
- 13 Narender T, Venkateswarlu K, Madhur G, Reddy KP. Synth. Commun. 2013; 43: 26
- 14 Cossy J, Albouy A, Scheloske M, Pardo DG. Tetrahedron Lett. 1994; 35: 1539
- 15 Vatèle J.-M. Tetrahedron 2002; 58: 5689
- 16 Marković D, Vogel P. Org. Lett. 2004; 6: 2693
- 17 Escoubet S, Gastaldi S, Timokhin VI, Bertrand MP, Siri D. J. Am. Chem. Soc. 2004; 126: 12343
- 18 Tsukamoto H, Suzuki T, Kondo Y. Synlett 2007; 3131
- 19 Schmidt B, Riemer M, Schilde U. Synlett 2014; 25: 2943
- 20 Schmidt B, Riemer M, Schilde U. Eur. J. Org. Chem. 2015; 7602
- 21 Schmidt B, Riemer M. Synthesis 2016; 48: 141
- 22 Iguchi D, Erra-Balsells R, Bonesi SM. Tetrahedron Lett. 2014; 55: 4653
- 23 Yoshida M, Fujino Y, Saito K, Doi T. Tetrahedron 2011; 67: 9993
- 24 Ghosh AK, Cheng X, Zhou B. Org. Lett. 2012; 14: 5046
- 25 Nawghare BR, Sakate SS, Lokhande PD. J. Heterocycl. Chem. 2014; 51: 291
- 26 Taylor C, Bolshan Y. Tetrahedron Lett. 2015; 56: 4392
- 27 Daskiewicz J.-B, Depeint F, Viornery L, Bayet C, Comte-Sarrazin G, Comte G, Gee JM, Johnson IT, Ndjoko K, Hostettmann K, Barron D. J. Med. Chem. 2005; 48: 2790
- 28 Ito F, Fusegi K, Kumamoto T, Ishikawa T. Synthesis 2007; 1785
- 29 Coombes CL, Moody CJ. J. Org. Chem. 2008; 73: 6758
- 30 Jeon J.-H, Kim MR, Jun J.-G. Synthesis 2011; 370
- 31 Lauer WM, Moe O. J. Am. Chem. Soc. 1943; 65: 289
- 32 Wunderli A, Winkler T, Hansen H.-J. Helv. Chim. Acta 1977; 60: 2436
- 33 Dallacker F, Sluysmans R. Monatsh. Chem. 1969; 100: 560
- 34 Molina P, Alajarin M, Vidal A. J. Org. Chem. 1990; 55: 6140
- 35 Mali RS, Massey AP. J. Chem. Res., Synop. 1998; 230
- 36 Freeman PW, Murphy ST, Nemorin JE, Taylor WC. Aust. J. Chem. 1981; 34: 1779
- 37 Mansoor F, Anis I, Khan A, Marasini BP, Choudhary MI, Shah MR. J. Asian Nat. Prod. Res. 2014; 16: 210
- 38 Jayshree N, Narayanan N, Sriram L. Asian J. Pharm. Clin. Res. 2012; 5: 101
- 39 Tasdemir D, Kaiser M, Brun R, Yardley V, Schmidt TJ, Tosun F, Rüedi P. Antimicrob. Agents Chemother. 2006; 50: 1352
- 40 Yoshida M, Fujino Y, Doi T. Org. Lett. 2011; 13: 4526
- 41 Kis Z, Closse A, Sigg HP, Hruban L, Snatzke G. Helv. Chim. Acta 1970; 53: 1577
- 42 Lin W.-Y, Teng C.-M, Tsai I.-L, Chen I.-S. Phytochemistry 2000; 53: 833
- 43 Lourenço TO, Akisue G, Roque NF. Phytochemistry 1981; 20: 773
- 44 Liu L.-L, Yang J.-L, Shi Y.-P. J. Asian Nat. Prod. Res. 2011; 13: 920
- 45 Rukachaisirikul V, Tansakul C, Saithong S, Pakawatchai C, Isaka M, Suvannakad R. J. Nat. Prod. 2005; 68: 1674
- 46 Stompor M, Dancewicz K, Gabryś B, Anioł M. J. Agric. Food Chem. 2015; 63: 6749
- 47 Gerlach U, Brendel J, Lang H.-J, Paulus EF, Weidmann K, Brüggemann A, Busch AE, Suessbrich H, Bleich M, Greger R. J. Med. Chem. 2001; 44: 3831
- 48 Lucas CL, Lygo B, Blake AJ, Lewis W, Moody CJ. Chem. Eur. J. 2011; 17: 1972
- 49 Mal K, Kaur A, Haque F, Das I. J. Org. Chem. 2015; 80: 6400
- 50 Zhu M, Kim MH, Lee S, Bae SJ, Kim SH, Park SB. J. Med. Chem. 2010; 53: 8760