A general synthetic route towards bastadins. Part 1: Synthesis of the eastern part of bastadins 4-16

Tetrahedron Letters

Volumn 40, Issue 38, 1999, Pages 7023-7026

  Couladouros, Elias A ^a,b   Moutsos, Vassilios I ^a,b  

^a AGRICULTURAL UNIVERSITY OF ATHENS   (Greece)

^b INSTITUTE OF NANOSCIENCE AND NANOTECHNOLOGY   (Greece)

Author keywords

Keto acids; Oximino acids; Bastadins; Iodonium salt; Natural products; Synthesis

Indexed keywords

2 OXOACID; BASTADIN 10; BASTADIN 11; BASTADIN 12; BASTADIN 14; BASTADIN 15; BASTADIN 16; BASTADIN 4; BASTADIN 5; BASTADIN 6; BASTADIN 7; BASTADIN 8; BASTADIN 9; ETHER DERIVATIVE; IODINE DERIVATIVE; MACROCYCLIC COMPOUND; NATURAL PRODUCT; OXOACID; UNCLASSIFIED DRUG;

ARTICLE; PARTIAL DRUG SYNTHESIS;

EID: 0033578771     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01429-X     Document Type: Article

References (39)

1. (a) Kazlauskas, R.; Lidgard, R. O.; Murphy, P. T.; Wells, R. J. Tetrahedron Lett. 1980, 21, 2277-2280;
2. (b) Kazlauskas, R.; Lidgard, R. O.; Murphy, P. T.; Wells, R. J.; Blount, J. F. Aust. J. Chem. 1981, 34, 765-786;
3. (c) Miao, S.; Andersen, R. J. J. Nat. Prod. 1990, 53, 1441-1446;
4. (d) Pordesimo, E. O.; Schmitz, F. J. J. Org. Chem. 1990, 55, 4704-4709;
5. (e) Butler, M. S.; Lim, T. K.; Capon, R. J.; Hammond, L. S. Aust. J. Chem. 1991, 44, 287-296;
6. (f) Dexter, A. F.; Garson, M. J. J. Nat. Prod. 1993, 56, 782-786;
7. (g) Carney, J. R.; Scheuer, P. J.; Kelly-Borges, M. J. Nat. Prod. 1993, 56, 153-157;
8. (h) Gulavita, N. K.; Wright, A. E.; McCarthy, P. J.; Pomponi, S. A.; Kelly-Borges, M.; Chin, M.; Sills, M. A. J. Nat. Prod. 1993, 56, 1613-1617;
9. (i) Park, S. K.; Jurek, J.; Carney, J. R.; Scheuer, P. J. J. Nat. Prod. 1994, 57, 407-410.
10. (a) Pettit, G. R.; Butler, M. S.; Bass, C. G.; Doubek, D. L.; Williams, M. D.; Schmidt, J. M.; Pettit, R. K.; Hooper, J. N. A.; Tackett, L. P.; Filiatraull, M. J. J. Nat. Prod. 1995, 58, 680-688;
11. (b) Jaspars, M.; Rali, T.; Laney, M.; Schatzman, R. C; Diaz, M. C.; Schmitz, F. J.; Pordesimo, E. O.; Crews, P. Tetrahedron 1994, 50, 7367-7374;
12. (c) Pessah, I. N.; Molinski, T. F.; Meloy, T. D.; Wong, P.; Buck, E. D.; Allen, P. D.; Mohr, F. C.; Mack, M. M. Am. J. Physiol. 1997, 272, C601-C614.
13. (a) Mack, M. M.; Molinski, T. F.; Buck, E. D.; Pessah, I. N. J. Biol. Chem. 1994, 269, 23236-23249;
14. (b) Franklin, M. A.; Penn, S. G.; Lebrilla, C. B.; Lam, T. H.; Pessah, I. N.; Molinski, T. F. J. Nat. Prod. 1996, 59, 1121-1127.
15. (a) Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1982, 23, 1281-1284;
16. (b) Nishiyama, S.; Suzuki, T.; Yamamura, S. Tetrahedron Lett. 1982, 23, 3699-3702;
17. (c) Nishiyama, S.; Suzuki, T.; Yamamura, S. Chem. Lett. 1982, 1851-1852;
18. (d) Guo, Z.-W.; Machiya, K.; Salamonczyk, G. M.; Sih, C. J. J. Org. Chem. 1998, 63, 4269-4276; see also: Noda, H.; Niwa, M.; Yamamura, S. Tetrahedron Lett. 1981, 22, 3247-3248.
19. (d)Guo, Z.-W.; Machiya, K.; Salamonczyk, G. M.; Sih, C. J. J. Org. Chem. 1998, 63, 4269-4276; see also: Noda, H.; Niwa, M.; Yamamura, S. Tetrahedron Lett. 1981, 22, 3247-3248.
20. (a) Couladouros, E. A.; Soufli, I. C. Tetrahedron Lett. 1994, 35, 4409-4412;
21. (b) Couladouros, E. A.; Soufli, I. C. Tetrahedron Lett. 1995, 36, 9369-9372;
22. (c) Couladouros, E. A.; Soufli, I. C.; Moutsos, V. I.; Chadha, R. K. Chem. Eur. J. 1998, 4, 33-13.
23. Bailey, K. L.; Molinski, T. F. J. Org. Chem. 1999, 64, 2500-2504 and references cited therein.
24. Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Li, H.; Bräse, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421-3422.
25. During our work a revised procedure for the conversion of triazenes to phenols was released (Nicolaou, K. C.; Takayanagi, M.; Jain, N. F.; Natarajan, S.; Koumbis, A. E.; Bando, T.; Ramanjulu, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2717-2719). However, application of this method on several model compounds was still yielding the undesired reduced compound as the main product.
26. (a) Beringer, F. M.; Drexler, M.; Gindler, E. M.; Lumpkin, C. C. J. Am. Chem. Soc. 1953, 75, 2705-2708;
27. (b) Beringer, F. M.; Brierley, A.; Drexler, M.; Gindler, E. M.; Lumpkin, C. C. ibid. 1953, 75, 2708-2712;
28. (c) Beringer, F. M.; Falk, R. A.; Karniol, M.; Lillien, I.; Masullo, G.; Mausner, M.; Sommer, E. J. Am. Chem. Soc. 1959, 81, 342-351;
29. (d) Dibbo, A.; Stephenson, L.; Walker, T.; Warburton, W. K. J. Chem. Soc. 1961, 2645-2651;
30. (e) Crowder, J. R.; Glover, E. E.; Grundon, M. F.; Kaempfen, H. X. J. Chem. Soc. 1963, 4578-1585;
31. (f) Hickey, D. M. B.; Leeson, P. D.; Novelli, R.; Shah, V. P.; Burpitt, B. E.; Crawford, L. P.; Davies, B. J.; Mitchell, M. B.; Pancholi, K. D.; Tuddenham, D.; Lewis, N. J.; O'Farrell, C. J. Chem. Soc., Perkin Trans. 1 1988, 3103-3111;
32. (g) Crimmin, M. J.; Brown, A. G. Tetrahedron Lett. 1990, 31, 2017-2020;
33. (h) Chakraborty, T. K.; Reddy, G. V. J. Org. Chem. 1992, 57, 5462-5469.
34. Satisfactory spectroscopic and HRMS data of all new compounds are available.
35. (a) Garegg, P. J.; Samuelsson, B. J. Chem. Soc., Chem. Commun. 1979, 978-980;
36. (b) Garegg, P. J.; Samuelsson B. J. Chem. Soc., Perkin Trans. 1 1980, 2866-2869.
37. (a) Shivers, J. C.; Hauser, C. R. J. Am. Chem. Soc. 1947, 69, 1264-1265;
38. (b) Okamoto, K. T.; Clardy, J. Tetrahedron Lett. 1987, 28, 4969-4972.
39. Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559-2562.