Temporary restraints to overcome steric obstacles: An efficient strategy for the synthesis of mycalamideB

Angewandte Chemie - International Edition

Volumn 49, Issue 46, 2010, Pages 8682-8685

  Jewett, John C ^a   Rawal, Viresh H ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

amides; DielsAlder reaction; MukaiyamaMichael reaction; mycalamideB; natural products

Indexed keywords

DIELS-ALDER REACTION; EFFICIENT STRATEGY; MUKAIYAMAMICHAEL REACTION; MYCALAMIDEB; NATURAL PRODUCTS; ONE POT; STEREOCENTERS;

AMIDES;

SYNTHESIS (CHEMICAL);

ACETAL DERIVATIVE; CARBAMIC ACID DERIVATIVE; ETHYLENE DERIVATIVE; ISOCYANIC ACID DERIVATIVE; KETENE; KETONE; MYCALAMIDE B; PYRAN DERIVATIVE;

ARTICLE; CHEMISTRY; SYNTHESIS;

ACETALS; CARBAMATES; ETHYLENES; ISOCYANATES; KETONES; PYRANS;

EID: 78149425383     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201003361     Document Type: Article

References (49)

1. For a general discussion of strategies in total synthesis, see
2. E. J. Corey, X.-M. Cheng, The Logic of Chemical Synthesis, Wiley, New York, 1995
3. K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis: Targets, Strategies, Methods, VCH-Publishers, New York, 1996
4. T. Hudlicky, J. W. Reed, The Way of Synthesis: Evolution of Design and Methods for Natural Products, Wiley-VCH, Weinheim, 2007.
5. PelorusideA:, L. M. West, P. T. Northcote, J. Org. Chem. 2000, 65, 445 449
6. Pateamine:, P. T. Northcote, J. W. Blunt, M. H. G. Munro, Tetrahedron Lett. 1991, 32, 6411 6414
7. 13-Deoxytedanolide:, N. Fusetani, T. Sugawara, S. Matsunaga, H. Hirota, J. Org. Chem. 1991, 56, 4971 4974.
8. For reviews, see
9. R. Narquizian, P. J. Kocienski, in The Role of Natural Products in Drug Discovery (Eds.:, J. Mulzer, R. Bohlmann,), Springer, New York, 2000, pp. 25 56
10. J. Piel, D. Butzke, N. Fusetani, D. Hui, M. Platzer, G. Wen, S. Matsunaga, J. Nat. Prod. 2005, 68, 472 479.
11. N. B. Perry, J. W. Blunt, M. H. G. Munro, L. K. Pannell, J. Am. Chem. Soc. 1988, 110, 4850 4851
12. N. B. Perry, J. W. Blunt, M. H. G. Munro, A. M. Thompson, J. Org. Chem. 1990, 55, 223 227.
13. N. S. Burres, J. J. Clement, Cancer Res. 1989, 49, 2935 2940.
14. MycalamideA
15. C. Y. Hong, Y. Kishi, J. Org. Chem. 1990, 55, 4242 4245
16. T. Nakata, H. Fukui, T. Nakagawa, H. Matsukura, Heterocycles 1996, 42, 159 164
17. W. R. Roush, L. A. Pfeifer, Org. Lett. 2000, 2, 859 862
18. J.-H. Sohn, N. Waizumi, H. M. Zhong, V. H. Rawal, J. Am. Chem. Soc. 2005, 127, 7290 7291
19. N. Kagawa, M. Ihara, M. Toyota, Org. Lett. 2006, 8, 875 878; Formal syntheses
20. T. Nakata, H. Matsukura, D. Jian, H. Nagashima, Tetrahedron Lett. 1994, 35, 8229 8232
21. B. M. Trost, H. Yang, G. D. Probst, J. Am. Chem. Soc. 2004, 126, 48 49.
22. The only previously reported total syntheses of mycalamideB are by Kishi, as described in Ref.[6a], and Kocienski, see
23. P. J. Kocienski, R. Narquizian, P. Raubo, C. Smith, F. T. Boyle, Synlett 1998, 869 872
24. P. J. Kocienski, R. Narquizian, P. Raubo, C. Smith, L. J. Farrugia, K. Muir, F. T. Boyle, J. Chem. Soc. Perkin Trans. 1 2000, 2357 2384.
25. Other members include
26. onnamideA:, C. Y. Hong, Y. Kishi, J. Am. Chem. Soc. 1991, 113, 9693 9694
27. theopeder in D:, M. E. Green, J. C. Rech, P. E. Floreancig, Angew. Chem. 2008, 120, 7427 7430
28. Angew. Chem. Int. Ed. 2008, 47, 7317 7320, and the references therein
29. pederin:, J. C. Jewett, V. H. Rawal, Angew. Chem. 2007, 119, 6622 6624
30. Angew. Chem. Int. Ed. 2007, 46, 6502 6504, and the references therein
31. theopederinB:, Y. Nishii, T. Higa, S. Takahashi, T. Nakata, Tetrahedron Lett. 2009, 50, 3597 3601
32. psymberin:, M. T. Crimmins, J. M. Stevens, G. M. Schaaf, Org. Lett. 2009, 11, 3990 3993, and the references therein. For a synthesis of the non-natural, 18-O-methyl mycalamideB, see
33. P. J. Kocienski, P. Raubo, J. K. Davis, F. T. Boyle, D. E. Davies, A. Richter, J. Chem. Soc. Perkin Trans. 1 1996, 1797 1808.
34. For examples of this coupling strategy for the trioxadecalin core see, Refs.[6a,b,d], and [8a,b,d].
35. For examples of this coupling strategy for the trioxadecalin core, see Refs.[6c,e], [7a,b], and [8f].
36. Other Lewis acids gave lower selectivities with only moderately better yields, and, owing to the difficulty of separating the diastereomers, MAD was deemed to be superior.
37. M. Oishi, S. Aratake, H. Yamamoto, J. Am. Chem. Soc. 1998, 120, 8271 8272.
38. S. Danishefsky, Acc. Chem. Res. 1981, 14, 400 406.
39. Silylketene acetal 12 was synthesized in an analogous fashion to the silylketene acetal used in our previous synthesis of pederin (Ref.[8c]). For further details, see the Supporting Information.
40. For a similar acetal formation, see Ref.[7a] and the references therein.
41. CCDC778951 (14) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
42. Kocienski et al. had reported good selectivity for the MPV reduction of a similar substrate at room temperature, but noted that heating the reaction to drive it to completion caused the selectivity to drop (see Ref.[7b]).
43. A. E. Greene, C. L. Drian, P. Crabbe, J. Am. Chem. Soc. 1980, 102, 7583 7584.
44. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley, Hoboken, 1999.
45. For a review, see:, R. W. Alder, Acc. Chem. Res. 1983, 16, 321 327.
46. T. Shioiri, K. Ninomiya, S. Yamada, J. Am. Chem. Soc. 1972, 94, 6203 6205.
47. D. A. Evans, T. C. Britton, J. A. Ellman, Tetrahedron Lett. 1987, 28, 6141 6144
48. D. A. Evans, S. W. Kaldor, T. K. Jones, J. Clardy, T. J. Stout, J. Am. Chem. Soc. 1990, 112, 7001 7031.
49. For the use of LiOH with LiCl to selectively cleave a carbamate in the presence of an amide bond in the context of carbohydrate synthesis, see:, P. Wei, R. J. Kerns, Tetrahedron Lett. 2005, 46, 6901 6905.