Total synthesis of (-)-microcarpalide, a novel microfilament disrupting metabolite

Organic and Biomolecular Chemistry

Volumn 2, Issue 1, 2004, Pages 38-47

  Davoli, Paolo ^a   Spaggiari, Alberto ^a   Castagnetti, Luca ^a   Prati, Fabio ^a  

^a UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; ESTERIFICATION; METABOLITES; OXIDATION; REACTION KINETICS; SYNTHESIS (CHEMICAL);

FUNGAL; MICROCARPALIDE; MICROFILAMENT; RING CLOSING METATHESIS;

ORGANIC COMPOUNDS;

INSERTION SEQUENCES;

ALKANE; MICROCARPALIDE; SINGLE HETEROCYCLIC RINGS;

ARTICLE; CHEMISTRY; DRUG EFFECT; MICROFILAMENT; STEREOISOMERISM; SYNTHESIS;

ALKANES; HETEROCYCLIC COMPOUNDS, 1-RING; MICROFILAMENTS; STEREOISOMERISM;

EID: 1642502980     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b308709c     Document Type: Article

References (57)

1. (a) J. Gusman and M. Vanhaelen, Recent Res. Dev. Phytochem., 2000, 4, 187-206
2. (b) R.-X. Tan and W.-H. Zou, Nat. Prod. Rep., 2001, 18, 448-459
3. (c) B. Schulz, C. Boyle, S. Draeger, A. K. Rommert and K. Krohn, Mycol. Res., 2002, 106, 996-1004.
4. For recent examples: (a) D. B. Stierle, A. A. Stierle and T. Bugni, J. Org. Chem., 2003, 68, 4966-4969
5. (b) G. Y. Chen, Y. C. Lin, L. Wen, L. L. P. Vrijmoed and E. B. G. Jones, Tetrahedron, 2003, 59, 4907-4909
6. (c) J. A. Findlay, G. Q. Li, J. D. Miller and T. O. Womiloju, Can. J. Chem., 2003, 81, 284-292
7. (d) A. Abdel-Lateff, C. Klemke, G. M. König and A. D. Wright, J. Nat. Prod., 2003, 66, 706-708
8. (e) P. Kongsaeree, S. Prabpai, N. Sriubolmas, C. Vongvein and S. Wiyakrutta, J. Nat. Prod., 2003, 66, 709-711
9. (f) B. Köpke, R. W. S. Weber and H. Anke, Phytochemistry, 2002, 60, 709-714
10. (g) G. Strobel, E. Ford, J. Worapong, J. K. Harper, A. M. Arif, D. M. Grant, P. C. W. Fung and R. M. W. Chau, Phytochemistry, 2002, 60, 179-183
11. (h) S. F. Brady, S. M. Bondi and J. Clardy, J. Am. Chem. Soc., 2001, 123, 9900-9901
12. (i) J. Y. Li, J. K. Harper, D. M. Grant, B. O. Tombe, B. Bashyal, W. M. Hess and G. A. Strobel, Phytochemistry, 2001, 56, 463-468.
13. A. S. Ratnayake, W. Y. Yoshida, S. L. Mooberry and T. Hemscheidt, Org. Lett., 2001, 3, 3479-3481.
14. B. Bodo, L. Molho, D. Davoust and D. Molho, Phytochemistry, 1983, 22, 447-451.
15. (a) A. Evidente, R. Lanzetta, R. Capasso, M. Vurro and A. Bottalico, Phytochemistry, 1993, 34, 999-1003
16. (b) A. Evidente, R. Capasso, M. A. Abouzeid, R. Lanzetta, M. Vurro and A. Bottalico, J. Nat. Prod., 1993, 56, 1937-1943.
17. A. Arnone, G. Assante, M. Montorsi, G. Nasini and E. Ragg, Gazz. Chim. Ital., 1993, 123, 71-73.
18. (a) A. Evidente, R. Lanzetta, R. Capasso, A. Andolfi, A. Bottalico, M. Vurro and M. C. Zonno, Phytochemistry, 1995, 40, 1637-1641
19. (b) A. Evidente, R. Lanzetta, R. Capasso, A. Andolfi, M. Vurro and M. C. Zonno, Phytochemistry, 1997, 44, 1041-1045
20. (c) A. Evidente, R. Capasso, A. Andolfi, M. Vurro and M. C. Zonno, Phytochemistry, 1998, 48, 941-945.
21. (a) J. F. Rivero-Cruz, G. García-Aguirre, C. M. Cerda-García-Rojas and R. Mata, Tetrahedron, 2000, 56, 5337-5344
22. (b) J. F. Rivero-Cruz, M. Macías, C. M. Cerda-García-Rojas and R. Mata, J. Nat. Prod., 2003, 66, 511-514.
23. (a) T. M. Trnka and R. H. Grubbs, Acc. Chem. Res., 2001, 34, 18-29
24. (b) A. Fürstner, Angew. Chem., Int. Ed., 2000, 39, 3012-3043
25. (c) R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413-4450.
26. (a) D. S. Matteson, Acc. Chem. Res., 1988, 21, 294-300
27. (b) D. S. Matteson, Chem. Rev., 1989, 89, 1535-1551
28. (c) D. S. Matteson, J. Organomet. Chem., 1999, 581, 51-65.
29. D. S. Matteson, K. M. Sadhu and M. L. Peterson, J. Am. Chem. Soc., 1986, 108, 810-819.
30. H. R. Snyder, J. A. Kuck and J. R. Johnson, J. Am. Chem. Soc., 1938, 60, 105-111.
31. (a) D. S. Matteson and D. Majumdar, J. Am. Chem. Soc., 1980, 102, 7588-7590
32. (b) D. S. Matteson and D. Majumdar, Organometallics, 1983, 2, 1529-1535.
33. (a) M. M. Midland, A. R. Zolopa and R. L. Halterman, J. Am. Chem. Soc., 1979, 101, 248-249
34. (b) D. S. Matteson, Acc. Chem. Res., 1970, 3, 186-193.
35. (a) D. S. Matteson and R. Ray, J. Am. Chem. Soc., 1980, 102, 7590-7591
36. (b) D. S. Matteson, R. Ray, R. R. Rocks and D. J. Tsai, Organometallics, 1983, 2, 1536-1543.
37. (a) H. C. Brown, in Boranes in Organic Chemistry, Cornell University Press, Ithaca, NY, 1972, pp. 317-409
38. (b) G. W. Kabalka, R. J. Newton, Jr. and J. Jacobus, J. Org. Chem., 1978, 43, 1567-1569.
39. M. Carmack and C. H. Kelley, J. Org. Chem., 1968, 33, 2171-2173.
40. P. W. Feit, J. Med. Chem., 1964, 7, 14-17.
41. J. Taunton, J. L. Collins and S. L. Schreiber, J. Am. Chem. Soc., 1996, 118, 10412-10422.
42. H. Iida, N. Imazaki and C. Kibayashi, J. Org. Chem., 1987, 52, 3337-3342.
43. S. Clough, M. E. Raggatt, T. J. Simpson, C. L. Willis, A. Whiting and S. K. Wrigley, J. Chem. Soc., Perkin Trans. 1, 2000, 2475-2481.
44. P. Schnurrenberger, E. Hungerbühler and D. Seebach, Liebigs Ann. Chem., 1987, 733-744.
45. During a preliminary approach to fragment B, diol 12 was treated with NaH and benzyl bromide in DMF at -40 °C to afford the corresponding monobenzyl derivative. In fact, a benzyl protection seemed convenient since it could have been removed en route, during the hydrogenation step that was planned to follow the first Wittig homologation. Surprisingly and unexpectedly, however, cleavage of the benzyl group by catalytic hydrogenation was found rather troublesome, even under higher pressures. Hence, annoyingly, the problem was circumvented by switching to a different protecting group for diol 12, namely TBDMS, and the synthetic sequence had to be lengthened by one step, i.e., deprotection with TBAF.
46. E. J. Corey and A. Venkateswarlu, J. Am. Chem. Soc., 1972, 94, 6190-6191.
47. (a) D. Batty and D. J. Crich, J. Chem. Soc., Perkin Trans. 1, 1992, 3193-3204
48. (b) D. Batty and D. J. Crich, Tetrahedron Lett., 1992, 33, 875-878.
49. J. Murga, E. Falomir, J. García-Fortanet, M. Carda and J. A. Marco, Org. Lett., 2002, 4, 3447-3449.
50. A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann and R. Mynott, J. Am. Chem. Soc., 2002, 124, 7061-7069.
51. D. Liu and S. A. Kozmin, Org. Lett., 2002, 4, 3005-3007.
52. A. Fürstner, O. Guth, A. Düffels, G. Seidel, M. Liebl, B. Gabor and R. Mynott, Chem.-Eur. J., 2001, 7, 4811-4820.
53. M. K. Gurjar, R. Nagaprasad and C. V. Ramana, Tetrahedron Lett., 2003, 44, 2873-2875.
54. E. J. Corey, J. L. Gras and P. Ulrich, Tetrahedron Lett., 1976, 11, 809-812.
55. M. F. Lappert, Chem. Rev., 1956, 56, 959-1064.
56. H. C. Brown, N. G. Bhat and V. Somayaji, Organometallics, 1983, 2, 1311-1316.
57. L. J. Rubin, H. A. Lardy and H. O. L. Fischer, J. Am. Chem. Soc., 1952, 74, 425-428.