Studies on the synthesis of durhamycin A: Stereoselective synthesis of a model aglycone

Organic Letters

Volumn 10, Issue 20, 2008, Pages 4613-4616

  Pragani, Rajan ^a   Roush, William R ^a  

^a Scripps Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDROXY 1 PHENYL 2 PROPANONE; ALDEHYDE; ALKADIENE; ALLENE; DRUG DERIVATIVE; DURHAMYCIN A; FATTY ALCOHOL; MITHRAMYCIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; TEMPERATURE;

ALDEHYDES; ALKADIENES; FATTY ALCOHOLS; MOLECULAR STRUCTURE; PLICAMYCIN; STEREOISOMERISM; TEMPERATURE;

EID: 58149173853     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8018727     Document Type: Article

References (58)

1. Remers, W. A. In The Chemistry of Antitumor Antibiotics; Wiley-Interscience: New York, 1979; pp 133-175.
2. Skarbek, J. D.; Speedie, M. K. In Antitumor Compounds of Natural Origin: Chemistry and Biochemistry; Aszalos, A., Ed.; CRC Press: Boca Raton, FL, 1981; Vol. 1, pp 191-235.
3. Remers, W. A.; Iyengar, B. S. In Cancer Chemotherapeutic Agents; Foye, W. O., Ed.; American Chemical Society: Washington, DC, 1995; pp 577-679.
4. Wohlert, S. E.; Künzel, E.; Machinek, R.; Méndez, C.; Salas, J. A.; Rohr, J. J. Nat. Prod. 1999, 62, 119.
5. Ogawa, H.; Yamashita, Y.; Katahira, R.; Chiba, S.; Iwasaki, T.; Ashizawa, T.; Nakano, H. J. Antibiot. 1998, 51, 261.
6. Katahira, R.; Uosaki, Y.; Ogawa, H.; Yamashita, Y.; Nakano, H.; Yoshida, M. J. Antibiot. 1998, 51, 267.
7. Lombó, F.; Menéndez, N.; Salas, J. A.; Méndez, C. Appl. Microbiol. Biotechnol. 2006, 73, 1.
8. Gao, X.; Mirau, P.; Patel, D. J. J. Mol. Biol. 1992, 223, 259.
9. Sastry, M.; Patel, D. J. Biochemistry 1993, 32, 6588.
10. Liu, C.; Chen, F.-M. Biochemistry 1994, 33, 1419.
11. Aich, P.; Dasgupta, D. Biochemistry 1995, 34, 1376.
12. Katahira, R.; Katahira, M.; Yamashita, Y.; Ogawa, H.; Kyogoku, Y.; Yoshida, M. Nucleic Acids Res. 1998, 26, 744.
13. Remsing, L. L.; González, A. M.; Nur-e-Alam, M.; Fernández-Lozano, M. J.; Braña, A. F.; Rix, U.; Oliveira, M. A.; Méndez, C.; Salas, J. A.; Rohr, J. J. Am. Chem. Soc. 2003, 125, 5745.
14. Remsing, L. L.; Bahadori, H. R.; Carbone, G. M.; McGuffie, E. M.; Catapano, C. V.; Rohr, J. Biochemistry 2003, 42, 8313.
15. Kumar, V.; Remers, W. A.; Bradner, W. T. J. Med. Chem. 1980, 23, 376.
16. Silva, D. J.; Kahne, D. E. J. Am. Chem. Soc. 1993, 115, 7962.
17. Baig, I; Perez, M.; Braña, A. F.; Gomathinayagam, R.; Damodaran, C.; Salas, J. A.; Méndez, C.; Rohr, J. J. Nat. Prod. 2008, 71, 199.
18. Jayasuriya, H.; Lingham, R. B.; Graham, P.; Quamina, D.; Herranz, L.; Genilloud, O.; Gagliardi, M.; Danzeisen, R.; Tomassini, J. E.; Zink, D. L.; Guan, Z.; Singh, S. B. J. Nat. Prod. 2002, 65, 1091.
19. We have published a synthesis of functionalized precursors for the oligosaccharides of durhamycins A (1) and B (2): Durham, T. B.; Roush, W. R. Org. Lett. 2003, 5, 1875.
20. Roush, W. R.; Michaelides, M. R.; Tai, D. F.; Lesur, B. M.; Chong, W. K. M.; Harris, D. J. J. Am. Chem. Soc. 1989, 111, 2984.
21. Roush, W. R.; Murphy, M. J. Org. Chem. 1992, 57, 6622.
22. Roush, W. R.; Hartz, R. A.; Gustin, D. J. J. Am. Chem. Soc. 1999, 121, 1990.
23. Littke, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343.
24. Servi, S. J. Org. Chem. 1985, 50, 5865.
25. Treatment of 11 with vinylmagnesium bromide afforded an enone which was susceptible to Michael adddition by MeNH(OMe) under the reaction conditions.
26. Luche, J.-L. J. Am. Chem. Soc. 1978, 100, 2226.
27. Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001.
28. 4 addition at -78 °C prior to warming the reaction mixture to 23 °C, large amounts of the hydrated form of aldehyde 13 were isolated.
29. Corey, E. J.; Yu, C.-M.; Lee, D.-H. J. Am. Chem. Soc. 1990, 112, 878.
30. Reactions ran on a 1.3 g scale (of 13) gave slightly lower diastereoselectivity (6:1 dr).
31. 2 or toluene led to elimination of the C(1′)-methoxy group, giving the corresponding diene, presumably by way of the allylic transposed allylborane isomer of 6.
32. Extending hydroboration reaction times beyond 10 min led to decreased diastereoselectivity (believed to originate from E/Z olefin 1,3-isomerization of 6 via the methallylic borane isomer) and lower yields.
33. (a) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1.
34. (b) Chemler, S. R.; Roush, W. R. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; pp 403.
35. Harrity, J. P.; Visser, M. S.; Gleason, J. D.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 1488.
36. Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130.
37. (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
38. (b) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
39. Lautens, M.; Hiebert, S. J. Am. Chem. Soc. 2004, 126, 1437.
40. Similar assignments by half-chair coupling constants: (a) Hobbs-Mallyon, D.; Li, W.; Whiting, D. A. J. Chem. Soc., Perkin Trans. 1 1997, 1511.
41. (b) Thorey, C.; Bouquillon, S.; Helimi, A.; Hénin, F.; Muzart, J. Eur. J. Org. Chem. 2002, 2151.
42. (a) For formation of (E)-allyl(diisopinocampheyl)boranes by room temperature allene hydroboration: Naria, G.; Brown, H. C. Tetrahedron Lett. 1997, 38, 219.
43. (b) For low-temperature formation of (Z)- and (E)- crotyl(diisopinocampheyl)boranes: Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 5919.
44. (c) For formation of a kinetic (Z)-silylallyl(diisopinocampheyl) borane by allene hydroboration and isomerization studies: Heo, J.-N.; Micalizio, G. C.; Roush, W. R. Org. Lett. 2003, 5, 1693.
45. (d) For a discussion concerning the 1,3-migration of allylboron species: Kramer, G. W.; Brown, H. C. J. Organomet. Chem. 1977, 132, 9.
46. Efforts to convert the benzylic alcohol to a halide, tosylate, or mesylate leaving group resulted in either elimination or cyclization of the TCE-protected alcohol to form a tetrahydrofuran.
47. 3SnH xanthate reductions, see: Nozaki, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 6125.
48. 3SnH reductions, see: Neumann, W. P. Synthesis 1987, 665.
49. Scholl, M.; Ding, S.; Lee, C. W.; Grabbs, R. H. Org. Lett. 1999, 1, 953.
50. Jacobson, R. M.; Clader, J. W. Synth. Commun. 1979, 9, 57.
51. Dess, P. B.; Martin, J. C. J. Am. Chem. Soc. 1978, 100, 300.
52. Fleming, J. J.; McReynolds, M. D.; Dubois, J. J. Am. Chem. Soc. 2007, 129, 9964.
53. Plietker, B. Synthesis 2005, 15, 2453.
54. Baskaran, S.; Das, J.; Chandrasekaran, S. J. Org. Chem. 1989, 54, 5182.
55. Ryoo, E. S.; Shin, D. H.; Han, B. H. J. Korean Chem. Soc. 1987, 31, 359.
56. Srinivasan, N. S.; Lee, D. G. Synthesis 1979, 7, 520.
57. Keto-hydroxylation of substrates (not shown) lacking the C(2′) ketone (and therefore incapable of forming hemiketals) gave 8-10:1 mixtures of C(2) acyloin epimers.
58. Hemiketal formation, analogous to that indicated here for 2, is well documented in the olivin series (e.g., ref 22 and Roush, W. R.; Briner, K.; Kesler, B. S.; Murphy, M.; Gustin, D. J. J. Org. Chem. 1996, 61, 6098).