Efficient total syntheses of (-)-colombiasin A and (-)-elisapterosin B: Application of the Cr-catalyzed asymmetric quinone Diels-Alder reaction

Angewandte Chemie - International Edition

Volumn 44, Issue 37, 2005, Pages 6046-6050

  Boezio, Alessandro A ^a   Jarvo, Elizabeth R ^a   Lawrence, Brian M ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

Asymmetric catalysis; Cycloaddition; Metathesis; Natural products; Quinones

Indexed keywords

ADDITION REACTIONS; CATALYSIS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ASYMMETRIC CATALYSIS; CYCLOADDITION; METATHESIS; NATURAL PRODUCTS; QUINONES;

CHROMIUM;

BENZOQUINONE; BENZOQUINONE DERIVATIVE; BRIDGED COMPOUND; CHROMIUM; COLOMBIASIN A; DITERPENE; ELISAPTEROSIN B;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BENZOQUINONES; BRIDGED COMPOUNDS; CHROMIUM; DITERPENES; MODELS, MOLECULAR; STEREOISOMERISM;

EID: 25144455069     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502178     Document Type: Article

References (48)

1. A. D. Rodríguez, Tetrahedron 1995, 51, 4571-4618.
2. I. I. Rodríguez, Y.-P. Shi, O. J. Garcia, A. D. Rodríguez, A. M. S. Mayer, J. A. Sanchez, E. Ortega-Barria, J. Gonzalez, J. Nat. Prod. 2004, 67, 1672-1680.
3. a) S. A. Look, W. Fenical, G. K. Matsumoto, J. Clardy, J. Org. Chem. 1986, 51, 5140-5145;
4. b) V. Roussis, Z. Wu, W. Fenical, S. A. Strobel, G. D. VanDuyne, J. Clardy, J. Org. Chem. 1990, 55, 4916-4922.
5. A. C. Kohl, R. G. Kerr, Mar. Drugs 2003, 1, 54-65.
6. a) A. D. Rodríguez, C. Ramirez, Org. Lett. 2000, 2, 507-510;
7. b) A. D. Rodríguez, C. Ramirez, I. I. Rodríguez, C. L. Barnes, J. Org. Chem. 2000, 65, 1390-1398;
8. c) A. D. Rodríguez, E. Gonzalez, S. D. Huang, J. Org. Chem. 1998, 63, 7083-7091.
9. Total syntheses of colombiasin A: a) K. C. Nicolaou, G. Vassilikogiannakis, W. Magerlein, R. Kranich, Angew. Chem. 2001, 113, 2543-2547;
10. Angew. Chem. Int. Ed. 2001, 40, 2482-2486;
11. b) K. C. Nicolaou, G. Vassilikogiannakis, W. Magerlein, R. Kranich, Chem. Eur. J. 2001, 7, 5359-5371;
12. c) elisapterosin B: A. I. Kim, S. D. Rychnovsky, Angew. Chem. 2003, 115, 1305-1308;
13. Angew. Chem. Int. Ed. 2003, 42, 1267-1270;
14. d) elisapterosin B: D. C. Harrowven, D. D. Pascoe, D. Demurtas, H. O. Bourne, Angew. Chem. 2005, 117, 1247-1248;
15. Angew. Chem. Int. Ed. 2005, 44, 1221-1222.
16. a) For a review of synthetic approaches toward elisabethin A, see: G. Zanoni, M. Franzini, Angew. Chem. 2004, 116, 4942-4946;
17. Angew. Chem. Int. Ed. 2004, 43, 4837-4841;
18. b) elisabethin A: T. J. Heckrodt, J. Mulzer, J. Am. Chem. Soc. 2003, 125, 4680-4681;
19. c) elisapterosin B: N. Waizumi, A. R. Stankovic, V. H. Rawal, J. Am. Chem. Soc. 2003, 125, 13022-13023.
20. For approaches toward colombiasin A, see : a) D. C. Harrowven, M. J. Tyte, Tetrahedron Lett. 2001, 42, 8709-8711;
21. b) J. H. Chaplin, A. J. Edwards, B. L. Flynn, Org. Biomol. Chem. 2003, 1, 1842-1844.
22. a) A. D. Rodríguez, Y.-P. Shi, Tetrahedron 2000, 56, 9015-9023;
23. b) for a discussion, see reference [3b].
24. a) R. S. Thornton, R. G. Kerr, J. Chem. Ecol. 2002, 28, 2083-2090;
25. b) W. O'Neal, J. R. Pawlik, Mar. Ecol. Prog. Ser. 2002, 240, 117-126.
26. See preceding paper in this issue: E. R. Jarvo, B. M. Lawrence, E. N. Jacobsen, Angew. Chem. 2005, 117, in press;
27. Angew. Chem. Int. Ed. 2005, 44, in press; DOI: 10.1002/anie.200502176.
28. K. Gademann, D. E. Chavez, E. N. Jacobsen, Angew. Chem. 2002, 114, 3185-3187;
29. Angew. Chem. Int. Ed. 2002, 41, 3059-3061.
30. For applications of the inverse electron demand HDA reaction in natural product synthesis, see: a) D. E. Chavez, E. N. Jacobsen, Org. Lett. 2003, 5, 2563-2565;
31. b) H. Gao, D. G. Hall, J. Am. Chem. Soc. 2005, 127, 1628-1629.
32. a) V. Boucard, K Larrieu, N. Lubin-Germain, J. Uziel, J. Augé, Synlett 2003, 1834-1837;
33. b) M. A. Tius, J. Gomez-Galeno, X.-Q. Gu, J. H. Zaidi, J. Am. Chem. Soc. 1991, 113, 5775-5783;
34. c) F. Tellier, R. Sauvetre, J.-F. Normant, J. Organomet. Chem. 1989, 364, 17-28;
35. d) P. Villiers, N. Vicart, Y. Ramondenc, G. Ple, Tetrahedron Lett. 1999, 40, 8781-8784.
36. M. Arisawa, Y. Torisawa, M. Nakagawa, Synthesis 1995, 1371-1372.
37. Although not required for the synthetic sequence, in situ oxidation of the cycloadduct to quinones 9 and 10 was performed to facilitate determination of the diastereo- and regioselectivity of the reaction by HPLC.
38. This would he predicted by reaction of a ground state conformation of diene 5 wherein allylic strain is minimized.
39. Formation of isomer 13′, wherein the olefin has isomerized to the tetrasubstituted silyl enol ether, presumably occurs during chromatographic purification. Analogous isomerizations are not observed with less hindered cycloadducts. See Supporting Information for details. For an example of isomerization of a silyl enol ether upon exposure to silica gel, see: P. Magnus, I. S. Mitchell, Tetrahedron Lett. 1998, 39, 9131-9134.
40. While this intermediate is quite stable under acidic conditions, it undergoes decomposition under basic conditions and upon chromatography on silica gel, presumably due to oxidation to the corresponding quinone.
41. Details of the crystal structure analysis are provided as Supporting Information. CCDC-263118 (14) 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.
42. 1H NMR spectra of subsequent intermediates.
43. A. K. Chatterjee, T.-L. Choi, D. P. Sanders, R. H. Grubbs, J. Am. Chem. Soc. 2003, 125, 11 360-11 370.
44. Catalyst 18 has been shown to be more tolerant to sulfur-containing functionality than previous generations of ruthenium-based metathesis catalysts; a) F. D. Toste, A. K. Chatterjee, R. H. Grubbs, Pure Appl. Chem. 2002, 74, 7-10;
45. b) G. Spagnol, M.-P. Heck, S. P. Nolan, C. Mioskowski, Org. Lett. 2002, 4, 1767-1770.
46. Attempts to effect deoxygenation of this intermediate led only to complex decomposition mixtures.
47. Access to tertiary alcohol 2 could prove interesting in synthetic routes toward other related natural products, such as elizabethin A. However, cross metathesis of quinone 16 with isoprene would serve as a shorter route to colombiasin A. Tandem cross-metathesis/qDA reactions did provide the desired product, but in consistently lower yields than the two-step cross-metathesis/ dehydration/qDA sequence. For examples of cross-metathesis reactions of conjugated dienes, see: T. W. Funk, J. Efskind, R. H. Grubbs, Org. Lett. 2005, 7, 187-190.
48. We are grateful to Professor A. D. Rodríguez of the University of Puerto Rico for kindly supplying a sample of natural colombiasin A.