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Synthesis 2016; 48(19): 3183-3198
DOI: 10.1055/s-0035-1562452
DOI: 10.1055/s-0035-1562452
paper
Diastereoselective Gold(I)-Catalyzed [2+2+2] Cycloaddition of Oxo-1,5-enynes
Weitere Informationen
Publikationsverlauf
Received: 21. Mai 2016
Accepted after revision: 13. Juni 2016
Publikationsdatum:
19. Juli 2016 (online)
‡ These authors contributed equally.
In memory of Professor Jean Normant.
Abstract
The intramolecular gold(I)-catalyzed [2+2+2] cycloaddition of oxo-1,5-enynes bearing protected homopropargylic alcohols provides access to oxatricyclic adducts with good to excellent diastereoselectivity.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562452.
- Supporting Information
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References
-
1a Zhang L, Sun J, Kozmin SA. Adv. Synth. Catal. 2006; 348: 2271
- 1b Fürstner A, Davies PW. Angew. Chem. Int. Ed. 2007; 46: 3410
- 1c Hashmi AS. K. Chem. Rev. 2007; 107: 3180
- 1d Li Z, Brouwer C, He C. Chem. Rev. 2008; 108: 3239
- 1e Arcadi A. Chem. Rev. 2008; 108: 3266
-
1f Jiménez-Núñez E, Echavarren AM. Chem. Rev. 2008; 108: 3326
- 1g Gorin DJ, Sherry BD, Toste FD. Chem. Rev. 2008; 108: 3351
-
1h Michelet V, Toullec PY, Genêt J.-P. Angew. Chem. Int. Ed. 2008; 47: 4268
-
1i Aubert C, Fensterbank L, Garcia P, Malacria M, Simonneau A. Chem. Rev. 2011; 111: 1954
- 1j Krause N, Winter C. Chem. Rev. 2011; 111: 1994
- 1k Obradors C, Echavarren AM. Acc. Chem. Res. 2014; 47: 902
- 1l Fensterbank L, Malacria M. Acc. Chem. Res. 2014; 47: 953
- 1m Dorel R, Echavarren AM. Chem. Rev. 2015; 115: 9028
- 2a Hashmi AS. K, Rudolph M. Chem. Soc. Rev. 2008; 37: 1766
- 2b Rudolph M, Hashmi AS. K. Chem. Commun. 2011; 47: 6536
-
2c Rudolph M, Hashmi AS. K. Chem. Soc. Rev. 2012; 41: 2448
- 2d Fürstner A. Acc. Chem. Res. 2014; 47: 925
- 2e Zhang Y, Luo T, Yang Z. Nat. Prod. Rep. 2014; 31: 489
- 3a Jiménez-Núñez E, Molawi K, Echavarren AM. Chem. Commun. 2009; 7327
-
3b Molawi K, Delpont N, Echavarren AM. Angew. Chem. Int. Ed. 2010; 49: 3517
- 3c Gaydou M, Miller RE, Delpont N, Ceccon J, Echavarren AM. Angew. Chem. Int. Ed. 2013; 52: 6396
- 3d Carreras J, Livendahl M, McGonigal PR, Echavarren AM. Angew. Chem. Int. Ed. 2014; 53: 4896
- 4 Jiménez-Núñez E, Claverie CK, Nieto-Oberhuber C, Echavarren AM. Angew. Chem. Int. Ed. 2006; 45: 5452
- 5 Obradors C, Echavarren AM. Chem. Eur. J. 2013; 19: 3547
- 6 Muratore ME, Homs A, Obradors C, Echavarren AM. Chem. Asian J. 2014; 9: 3066
- 7 Jiménez T, Carreras J, Ceccon J, Echavarren AM. Org. Lett. 2016; 18: 1410
- 8a Faustino H, Alonso I, Mascareñas JL. Angew. Chem. Int. Ed. 2013; 52: 6526
- 8b Faustino H, Varela I, Mascareñas JL, López F. Chem. Sci. 2015; 6: 2903
- 9 Zhou Q, Chen X, Ma D. Angew. Chem. Int. Ed. 2010; 49: 3513
- 10 Kobayashi M, Yasuzawa T, Kyogoku Y, Kido M, Kitagawa I. Chem. Pharm. Bull. 1982; 30: 3431
- 11 Jiang C.-H, Bhattachrayya A, Sha C.-K. Org. Lett. 2007; 9: 3241 ; and references therein
- 12 Huguet N, Echavarren AM. Synlett 2012; 23: 49
- 13 In this case the addition of methanol to the ketone as well as dimethyl acetal formation on the aldehyde was observed exclusively.
- 14 CCDC 1481203 (anti-8a), CCDC 1481204 (anti-8b), CCDC 1483401 (syn-8c), CCDC 1481205 (anti-8g) and CCDC 1481206 (9) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
- 15 López-Carrillo V, Huguet N, Mosquera Á, Echavarren AM. Chem. Eur. J. 2011; 17: 10972
- 16a Wilson MS, Woo JC. S, Dake GR. J. Org. Chem. 2006; 71: 4237
- 16b Yang M, Dong H, Jiang J, Wang M. Molecules 2015; 20: 21023
- 17 Zhong Y.-L, Shing TK. M. J. Org. Chem. 1997; 62: 2622
For reviews on the total synthesis of natural products using gold(I) catalysis, see:
See our previous reports on the total synthesis of terpenoids using gold(I) catalysis: