Erratum: Formal asymmetric synthesis of echinopine A and B (Angewandte Chemie - International Edition (2011) 50 DOI: 10.1002/anie.201008000);Formal asymmetric synthesis of echinopine A and B

Angewandte Chemie - International Edition

Volumn 50, Issue 13, 2011, Pages 3013-3016

  Peixoto, Philippe A ^a   Severin, Rene ^a   Tseng, Chih Chung ^a   Chen, David Y K ^a  

^a INSTITUTE OF CHEMICAL AND ENGINEERING SCIENCES   (Singapore)

Author keywords

Cascade reactions; Diels Alder reaction; Natural products; Terpenoids; Total synthesis; cascade reactions; natural products; terpenoids; total synthesis

Indexed keywords

CHEMICAL ENGINEERING; CHEMISTRY;

CASCADE REACTIONS; DIELS-ALDER REACTION; NATURAL PRODUCTS; TERPENOIDS; TOTAL SYNTHESIS;

CHEMICAL REACTIONS;

EID: 79952689942     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201207026     Document Type: Erratum

References (25)

1. M. Dong, B. Cong, S.-H. Yu, F. Sauriol, C.-H. Huo, Q.-W. Shi, Y.- C. Gu, L. O. Zamir, H. Kiyota, Org. Lett. 2008, 10, 701-704.
2. a) T. Magauer, J. Mulzer, K. Tiefenbacher, Org. Lett. 2009, 11, 5306-5309;
3. b) K. C. Nicolaou, H. Ding, J.-A. Richard, D. Y.-K. Chen, J. Am. Chem. Soc. 2010, 132, 3815-3818.
4. K. C. Nicolaou, S. A. Snyder, T. Montagnon, G. Vassilikogiannakis, Angew. Chem. 2002, 114, 1742-1773;
5. Angew. Chem. Int. Ed. 2002, 41, 1668-1698.
6. V. Michelet, P. Y. Toullec, J.-P Genet, Angew. Chem. 2008, 120, 4338-4386;
7. Angew. Chem. Int. Ed. 2008, 47, 4268-4315.
8. For a recent review on cascade reactions in total synthesis, see: a) K. C. Nicolaou, T. Montagnon, S. A. Snyder, Chem. Commun. 2003, 551-564;
9. b) L. F. Tietze, G. Brasche, K. M. Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006, p. 617;
10. c) K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292-7344;
11. Angew. Chem. Int. Ed. 2006, 45, 7134-7186.
12. a) A. Hosomi, M. Endo, H. Sakurai, Chem. Lett. 1976, 941-942;
13. b) I. Fleming, Org. React. 1989, 37, 57-575;
14. c) I. Fleming, Comprehensic Organic Synthesis, Vol. 6, Pergamon, Oxford, 1991, pp. 563-593.
15. K. Takeishi, K. Sugishima, K. Sasaki, K. Tanaka, Chem. Eur. J. 2004, 10, 5681-5688.
16. H. Lindlar, R. Dubuis, Org. Synth. Coll. Vol. 5 1973, 880-883.
17. K.-I. Imamura, E. Yoshikawa, V. Gevorgyan, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 5339-5340.
18. R. M. Beesley, C. K. Ingold, J. F. Thorpe, J. Chem. Soc. Trans. 1915, 107, 1080-1106.
19. J. Elings, H. Lempers, R. Sheldon, Eur. J. Org. Chem. 2000, 1905-1911.
20. Having demonstrated the feasibility of this novel approach to access late-stage intermediates 27 and 5, several end-game strategies leading to echinopines A (1) and B (2) involving pedestrian functional transformations could be conceived, and these studies will be reported in the full account of this work.
21. a) Y. Nagao, W.-M. Dai, M. Ochiai, S. Tsukagochi, E. Fujita, J. Am. Chem. Soc. 1988, 110, 289-291;
22. b) M. T. Crimmins, B. W. King, E. A. Tabet, K. Chaudhary, J. Org. Chem. 2001, 66, 894-902;
23. c) J. Patel, G. Clave, P.-Y. Renard, X. Franck, Angew. Chem. 2008, 120, 4292-4295;
24. Angew. Chem. Int. Ed. 2008, 47, 4224-4227.
25. In comparison to the previously reported total syntheses of the echinopines, where a [5,5]→[5,5,7]→[3,5,5,7] (reference [2a]) and a [5]→[3,5,5,]→[3,5,5,7] (reference [2b]) ring-forming sequence were executed, we demonstrated herein a conceptually contrasting sequence involving a one-pot preparation of a [5,6,7] system and its conversion to the [5,5,7] ring framework.