Asymmetric synthesis of the 1-epi aglycon of the cripowellins A and B

Angewandte Chemie - International Edition

Volumn 44, Issue 24, 2005, Pages 3766-3769

  Enders, Dieter ^a   Lenzen, Achim ^a   Raabe, Gerhard ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Alkaloids; Asymmetric syntheses; Heck reactions; Insecticides; Ring closing metatheses

Indexed keywords

REACTION KINETICS; SYNTHESIS (CHEMICAL);

ASYMMETRIC SYNTHESIS; HECK REACTION; RING-CLOSING METATHESIS (RCM);

AROMATIC COMPOUNDS;

AMARYLLIDACEAE ALKALOID; CRIPOWELLIN A; CRIPOWELLIN A 1 EPI AGLYCON; CRIPOWELLIN A 1-EPI AGLYCON; CRIPOWELLIN B;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALKYLATION; AMARYLLIDACEAE ALKALOIDS; CYCLIZATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 20444461257     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200500556     Document Type: Article

References (60)

1. Representative reviews about the Amaryllidaceue alkaloids: a) O. Hoshino in The Alkaloids, Vol. 51 (Ed.: G. A. Cordell), Academic Press, New York, 1998, pp. 324-424;
2. b) S. F. Martin in The Alkaloids. Vol. 30 (Ed.: A. Brossi), Academic Press, New York. 1987, pp. 251-376;
3. c) C. Fuganti in The Alkaloids, Vol. 15 (Ed.: R. H. F. Manske), Academic Press, London, 1975, pp. 83-164.
4. M. Gehling, A. Göhrt, D. Gondol, J. Lenz, O. Lockhoff, H.-F. Moeschler, R. Velten, D. Wendisch, W. Andersch, C. Erdelen, A. Harder, N. Mencke, A. Turberg, U. Wachendorff-Neumann (Bayer AG), DE 196 10 27A1, 1997 [Chem. Abstr. 1997, 127, 278406].
5. R. Velten, C. Erdelen, M. Gehling, A. Göhrt, D. Gondol, J. Lenz, O. Lockhoff, U. Wachendorff, D. Wendisch, Tetrahedron Lett. 1998, 39, 1737-1740.
6. Researchers at Bayer AG have determined that cripowellins A and B are neither acetylcholin esterase inhibitors nor PP1 inhibitors (personal communication).
7. T. Lindel, Nachr. Chem. Tech. Lab. 1997, 45, 775-779.
8. Review; H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547.
9. Prepared by esterification of the known alcohol with paramethoxybenzoic acid chloride (87% yield): J. A. Rao, M. P. Cava, J. Org. Chem. 1989, 54, 2751-2753.
10. The asymmetric dihydroxylation of allylic alcohols normally proceeds with only moderate enantioselectivity, in contrast to the reaction of the corresponding para-methoxybenzoic acid esters: E. J. Corey, A. Guzman-Perez, M. C. Noe, J. Am. Chem. Soc. 1995, 117, 10805-10816.
11. The enantiomeric excess was determined by HPLC on a chiral stationary phase. For this, ent-4 was prepared analogously to 4 but using AD-mix α instead.
12. Representative reviews on ring-closing metathesis: a) A. Deiters, S. F. Martin, Chem. Rev. 2004, 104, 2199-2238;
13. b) R. R. Schrock, A. H. Hoveyda, Angew. Chem. 2003, 115, 4740-4782;
14. Angew. Chem. Int. Ed. 2003, 42, 4592-4633;
15. c) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172;
16. Angew. Chem. Int. Ed. 2000, 39, 3012-3043;
17. d) M. E. Maier, Angew. Chem. 2000, 112, 2153-2157;
18. Angew. Chem. Int. Ed. 2000, 39, 2073-2077;
19. e) S. Blechert, Pure Appl. Chem. 1999, 71, 1393-1399;
20. f) A. Fürstner, Top. Organomet. Chem. 1998, 1, 37-72;
21. g) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450;
22. h) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2145;
23. Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055;
24. i) H.-G. Schmalz, Angew. Chem. 1995, 107, 1981-1984;
25. Angew. Chem. Int. Ed. Engl. 1995, 34, 1833-1836;
26. j) F.-X. Felpin, J. Lebreton, Eur. J. Org. Chem. 2003, 3693-3712.
27. For the synthesis of nine-membered rings with similar conformational constraints similar to those of the dioxolane ring by metathesis, see: a) P. W. R. Harris, M. A. Brimble, P. D. Gluckman, Org. Lett. 2003, 5, 1847-1850;
28. b) J. S. Clark, F. Marlin, B. Nay, C. Wilson, Org. Lett. 2003, 5, 89-92;
29. c) K. P. Kaliappan, N. Kumar, Tetrahedron Lett. 2003, 44, 379-381;
30. d) M. Hirama, T. Oishi, H. Uehara, M. Inoue, M. Maruyama, H. Oguri, M. Satake, Science 2001, 294, 1904-1907;
31. c) J. S. Clark, O. Hamelin, Angew. Chem. 2000, 112, 380-382;
32. Angew. Chem. Int. Ed. 2000, 39, 372-374;
33. f) S. J. Bamford, K. Goubitz, H. L. van Lingen, T. Luker, H. Schenk, H. Hiemstra, J. Chem. Soc. Perkin Trans. 1 2000, 345-351;
34. g) T. Oishi, Y. Nagumo, M. Hirama, Chem. Commun. 1998, 1041-1042;
35. h) M. Delgado, J. D. Martín, Tetrahedron Lett. 1997, 38, 6299-6300.
36. For secondary and tertiary amides in ring-closing metatheses, see: a) A. J. Brouwer, R. M. J. Liskamp, J. Org. Chem. 2004, 69, 3662-3668;
37. b) L. Banfi, A. Basso, G. Guanti, R. Riva, Tetrahedron Lett. 2003, 44, 7655-7658.
38. There are only very few examples for the synthesis of nine-memhered rings by methathesis without conformational constraints. They are limited almost exclusively to nine-membered cyclic ethers for which the gauche effect can be exploited: a) M. T. Crimmins, M. T. Powell. J. Am. Chem. Soc. 2003, 125, 7592-7595;
39. b) M. T. Crimmins, K. A. Emmitte, A. L. Choy, Tetrahedron 2002, 58, 1817-1834;
40. c) Y. Baba, G. Saha, S. Nakao, C. Iwata, T. Tanaka, T. Ibuka, H. Ohishi, Y. Takemoto, J. Org. Chem. 2001, 66, 81-88;
41. d) M. T. Crimmins, A. L. Choy, J. Org. Chem. 1997, 62, 7548-7549.
42. Representative reviews on the Heck reaction: a) S. Bräse, A. de Meijere in Metal-Catalyzed Cross-Coupling Reactions, 2nd ed. (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004, pp. 217-315;
43. b) J. T. Link, L. E. Overman in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 231-269;
44. c) A. B. Dounay, L. E. Overman, Chem. Rev. 2003, 103, 2945-2963;
45. d) J. T. Link in Organic Reactions, Vol. 60 (Eds.: L. E. Overman), Wiley, New York, 2002, pp. 157-534;
46. e) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473-2506;
47. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411.
48. Apart from 12, minor amounts of 11 could also be isolated when the Heck reaction was performed under cationic conditions (in the crude product the ratio 12/11 was determined to be 8.2:1 by means of gas chromatography). However, 11 could be easily separated from 12 by column chromatography on silica gel because of its higher polarity.
49. After 4 h (complete conversion): E/Z = 1:1.7; after 24 z: E/Z = 1:1 (determined by gas chromatography).
50. The relative configurations were determined by NOE measurements.
51. For the synthesis of bicyclic systems by a sequence of RCM and Heck reactions, see: a) M. Lautens, V. Zunic, Can. J. Chem. 2004, 82, 399-407;
52. b) R. Grigg, M. York, Tetrahedron Lett. 2000, 41, 7255-7258;
53. c) R. Grigg, V. Sridharan, M. York, Tetrahedron Lett. 1998, 39, 4139-4142.
54. J. D. White, T. C. Somers, J. Am. Chem. Soc. 1994, 116, 9912-9920.
55. G. A. Molander, G. Hahn, J. Org. Chem. 1986, 51, 1135-1138.
56. G. A. Molander in Organic Reactions, Vol. 46 (Ed.: L. A. Paquette), Wiley, New York, 1994, pp. 211-367.
57. CCDC 263133 (16) contains 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/data_request/cif.
58. We will report separately on our alternative synthetic approaches to the cripowellins in detail: K. Catlin, RWTH Aachen, unpublished results;
59. C. Janeck, Ph.D. Thesis, RWTH Aachen, 2000;
60. M. Backes, Ph.D. Thesis, RWTH Aachen, 2004.