An enantioselective access to an anthracycline AB synthon by a desymmetrizing Heck cyclization

Synlett

Volumn , Issue 18, 2006, Pages 2965-2968

  Oestreich, Martin ^a   Sempere Culler, Fernando ^a   Machotta, Axel B ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Asymmetric synthesis; Catalysis; Cyclizations; Heck reaction; Palladium

Indexed keywords

ANTHRACYCLINE;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HECK REACTION; HYDROXYLATION;

EID: 33751275280     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-944193     Document Type: Article

References (39)

1. Minotti, G.; Menna, P.; Salvatorelli, E.; Cairo, G.; Gianni, L. Pharmacol. Rev. 2004, 56, 185; and references cited therein.
2. For tetracycline antibiotics, see: Charest, M. G.; Lerner, C. D.; Brubaker, J. D.; Siegel, D. R.; Myers, A. G. Science 2005, 308, 395.
3. (a) Krohn, K. Angew. Chem., Int. Ed. Engl. 1986, 25, 790;
4. Angew. Chem. 1986, 98, 788.
5. (b) Krohn, K. Tetrahedron 1990, 46, 291.
6. (a) Wong, C. M.; Popien, D.; Schwenk, R.; Te Raa, J. Can. J. Chem. 1971, 49, 2712.
7. (b) Arcamone, F.; Bernardi, L.; Patelli, B.; Giardino, P.; Di Marco, A.; Casazza, A. M.; Soranzo, C.; Pratesi, G. Experientia 1978, 34, 1255.
8. For recent total syntheses of aglycone 3, see: (a) Allen, J. G.; Hentemann, M. F.; Danishefsky, S. J. J. Am. Chem. Soc. 2000, 122, 571.
9. (b) Achmatowicz, O.; Szechner, B. J. Org. Chem. 2003, 68, 2398.
10. Sharpless asymmetric epoxidation/kinetic resolution: (a) Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. Tetrahedron 1984, 40, 4643.
11. (b) Holland, H. L.; Viski, P. J. Org. Chem. 1991, 56, 5226.
12. Sharpless asymmetric epoxidation: (c) Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497.
13. (d) Sodeoka, M.; Iimori, T.; Shibasaki, M. Chem. Pharm. Bull. 1991, 39, 323.
14. Sharpless asymmetric dihydroxylation: (e) Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807.
15. (f) Badalassi, F.; Crotti, P.; Di Bugno, C.; D'Arata, F.; Favero, L.; Ramacciotti, A. Tetrahedron: Asymmetry 2001, 12, 3155; and references cited therein.
16. Catalytic asymmetric ring-opening of a meso-epoxide: Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron 2002, 58, 75.
17. For recent reviews, see: (a) Intramolecular Heck reactions: Link, J. T. In Organic Reactions, Vol. 60; Overman, L. E., Ed.; Wiley: New York, 2002, 157.
18. (b) Catalytic asymmetric Heck reactions: Shibasaki, M.; Vogl, E. M.; Ohshima, T. Adv. Synth. Catal. 2004, 346, 1533.
19. (c) Heck reactions in total synthesis: Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945.
20. For desymmetrizing Heck cyclizations, see: (a) Ohrai, K.; Kondo, K.; Sodeoka, M.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 11737.
21. (b) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184.
22. (c) Lautens, M.; Zunic, V. Can. J. Chem. 2004, 82, 399.
23. (d) Bräse, S. Synlett 1999, 1654.
24. Oestreich, M.; Sempere-Culler, F.; Machotta, A. B. Angew. Chem. Int. Ed. 2005, 44, 149;
25. Angew. Chem. 2005, 117, 152.
26. For related work, see: Coogan, M. P.; Pottenger, M. J. J. Organomet. Chem. 2005, 690, 1409.
27. Machotta, A. B.; Sempere-Culler, F.; Straub, B. F.; Oestreich, M. manuscript in preparation.
28. Oestreich, M. Eur. J. Org. Chem. 2005, 783.
29. For neighboring group effects in intermolecular Heck reactions, see: (a) Díaz Buezo, N.; Alonso, I.; Carretero, J. C. J. Am. Chem. Soc. 1998, 120, 7129.
30. (b) Nilsson, P.; Larhed, M.; Hallberg, A. J. Am. Chem. Soc. 2003, 125, 3430.
31. Baeyer-Villiger oxidation of the corresponding benzaldehyde afforded the phenol in high yield: Wriede, U.; Fernandez, M.; West, K. F.; Harcourt, D.; Moore, H. W. J. Org. Chem. 1987, 52, 4485.
32. Applications of the 2-tetrahydropyranyl ether as an ortho-directing group are scarce: Geneste, H.; Schäfer, B. Synthesis 2001, 2259.
33. Snieckus, V. Chem. Rev. 1990, 90, 879.
34. Velkov, J.; Mincheva, Z.; Bary, J.; Boireau, G.; Fujier, C. Synth. Commun. 1997, 27, 375.
35. Oestreich, M.; Sempere-Culler, F. Chem. Commun. 2004, 692.
36. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
37. 3 (4.0 equiv) or TMP (4.0 equiv). Then a solution of triflate 9 and degassed toluene (0.1 M) is subsequently added. The resulting suspension is vigorously stirred at r.t. until the formation of a red homogeneous solution except for the solid base. The tube is sealed and heated at the indicated temperature for 18 h. After cooling to r.t., silica gel is added and the solvent is evaporated under reduced pressure. The crude product 8 on silica gel is subjected to flash column chromatography on silica gel using cyclohexane-tert-butylmethylether solvent mixtures.
38. 6S: C, 61.91; H, 5.20; S, 5.70. Found: C, 62.13; H, 5.37; S, 5.58.
39. 3: 412.2044; found: 412.2039.