Asymmetric syntheses of pectenotoxins-4 and -8, Part I: Synthesis of the C1-C19 subunit

Angewandte Chemie - International Edition

Volumn 41, Issue 23, 2002, Pages 4569-4573

  Evans, David A ^a   Rajapakse, Hemaka A ^a   Stenkamp, Dirk ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CHEMICAL ANALYSIS; ETHERS; INDUSTRIAL POISONS; MARINE COUPLINGS; MARINE POLLUTION; OLEFINS;

BIOLOGICAL ACTIVITY;

SYNTHESIS (CHEMICAL);

EPOXIDE; LACTONE; MACROLIDE; MARINE TOXIN; NATURAL PRODUCT; PECTENOTOXIN 4; PECTENOTOXIN 8; PECTENOTOXIN-4; PECTENOTOXIN-8; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CANCER CELL CULTURE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; CYTOTOXICITY; DRUG ISOLATION; HUMAN; HUMAN CELL; MARINE ENVIRONMENT; SYNTHESIS;

ALKYLATION; EPOXY COMPOUNDS; LACTONES; MACROLIDES; MARINE TOXINS; PYRANS;

EID: 0037011207     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021202)41:23<4569::AID-ANIE4569>3.0.CO;2-V     Document Type: Article

References (41)

1. a) T. Yasumoto, M. Murata, Y. Oshima, M. Sano, G. K. Matsumoto, J. Clardy, Tetrahedron 1985, 41, 1019-1025;
2. b) K. Sasaki, J. L. C. Wright, T. Yasumoto, J. Org. Chem. 1998, 63, 2475-2480;
3. c) J. H. Jung, C. J. Sim, C.-O. Lee, J. Nat. Prod. 1995, 58, 1722-1726;
4. d) M. Daiguji, M. Satake, K. J. James, A. Bishop, L. Mackenzie, H. Naoki, T. Yasumoto, Chem. Lett. 1998, 653-654.
5. a) S. Amano, K. Fujiwara, A. Murai, Synlett 1997, 1300-1302;
6. b) D. Awakura, K. Fujiwara, A. Murai, Synlett 2000, 1733-1736;
7. c) G. C. Micalizio, W. R. Roush, Org. Lett. 2001, 3, 1949-1952;
8. d) L. A. Paquette, X. Peng, D. Bondar, Org. Lett. 2002, 4, 937-940.
9. D. A. Evans, H. A. Rajapakse, A. Chiu, D. Stenkamp, Angew. Chem. 2002, 114, 4755; Angew. Chem. Int. Ed. 2002, 41, 4573.
10. D. A. Evans, H. A. Rajapakse, A. Chiu, D. Stenkamp, Angew. Chem. 2002, 114, 4755; Angew. Chem. Int. Ed. 2002, 41, 4573.
11. For similar bond constructions in a complex setting see: a) D. A. Evans, S. L. Bender, J. Morris, J. Am. Chem. Soc. 1988, 110, 2506-2526;
12. b) D. A. Evans, R. P. Polniaszek, K. M. DeVries, D. E. Guinn, D. J. Mathre, J. Am. Chem. Soc. 1991, 113, 7613-7630.
13. For the use of N-phenylamides as carboxyl surrogates see: a) D. A. Evans, P. H. Carter, E. M. Carreira, J. A. Prunet, M. Lautens, J. Am. Chem. Soc. 1999, 121, 7540-7552;
14. b) D. A. Evans, D. M. Fitch, T. E. Smith, V. J. Cee, J. Am. Chem. Soc. 2000, 122, 10033-10046.
15. D. A. Evans, D. W. C. MacMillan, K. R. Campos, J. Am. Chem. Soc. 1997, 119, 10859-10860.
16. Abbreviations: OTf = trifluoromethanesulfonyl; Bn = benzyl, TBS = tert-butyldimethylsilyl; d.r. = diastereomeric ratio; TES = triethylsilyl; lut. = 2,6-lutidine; PMB = 4-methoxybenzyl; DMSO = dimethyl sulfoxide; LiDBB = lithium di-tert-butyl biphenylide; DMAP = 4-(N, N-dimethylamino)pyridine; AIBN = 2,2′-azobisisobutyronitrile; TBODPS = tert-butoxydiphenylsilyl; Im = imidazole; PPTS = pyridinium para-toluenesulfonate; DMF = dimethylformamide; CSA = camphorsulfonic acid; TBHP = tert-butyl hydroperoxide; DET = diethyl tartrate: MS = molecular sieves.
17. D. A. Evans, K. A. Scheidt, J. N. Johnston, M. C. Willis, J. Am. Chem. Soc. 2001, 123, 4480-4491.
18. D. A. Evans, J. Bartroli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127-2129.
19. a) J. Godoy, S. V. Ley, B. Lygo, J. Chem. Soc. Chem. Commun. 1984, 1381-1382;
20. b) D. Culshaw, P. Grice, S.V. Ley, G.A. Strange, Tetrahedron Lett. 1985, 26, 5837-5840.
21. T. Fukuyama, S.-L. Lin, L. Li, J. Am. Chem. Soc. 1990, 112, 7050-7051;
22. See also: D. A. Evans, B. W. Trotter, P. J. Coleman, B. Cote, L. Carlos Dias, H. A. Rajapakse, A. N. Tyler, Tetrahedron 1999, 55, 8671-8726.
23. The typical conditions of adding iPrMgCl to a cooled solution of ester and MeNHOMe·.HCl resulted in the formation of significant amounts of isopropyl ketone. Preforming the magnesium amide of the Weinreb salt, thus ensuring that all the Grignard reagent was consumed prior to ester addition, was critical for the success of this reaction. For the original procedure, see: J. M. Williams, R. B. Jobson, N. Yasuda, G. Marchesini, U.-H. Dolling, E. J. Grabowski, Tetrahedron Lett. 1995, 36, 5461-5464.
24. M. T. Reetz, K. Kesseler, J. Org. Chem. 1985, 50, 5434-5436.
25. a) H. P. Wessel, T. Iversen, D. R. Bundle, J. Chem. Soc. Perkin Trans. 1 1985, 2247-2250;
26. b) N. Nakajima, K. Horita, R. Abe, O. Yonemitsu, Tetrahedron Lett. 1988, 29, 4139-4142.
27. A.-M. Faucher, C. Brochu, S. R. Landry, I. Duchesne. S. Hantos, A. Roy, A. Myles, C. Legault, Tetrahedron Lett. 1998, 39, 8425-8428.
28. N. T. Ahn, O. Einstein, Nouv. J. Chim. 1977, 1, 61-70.
29. Attempts to access aldehyde 17 directly by half reduction with electrophilic reagents such as diisobutylaluminum hydride resulted in N-phenylamide decomposition. This was the only reagent incompatibility observed throughout the synthesis.
30. J. R. Parikh, W. von E. Doering, J. Am. Chem. Soc. 1967, 89, 5505-5507.
31. 2 to vinyllithium 14b. See: M. Nakatsuka, J. A. Ragan, T. Sammakia, D. B. Smith, D. E. Uehling, S. L. Schreiber, J. Am. Chem. Soc. 1990, 112, 5583-5601.
32. a) P. K. Freeman, L. L. Hutchinson, J. Org. Chem. 1980, 45, 1924-1930;
33. b) R. E. Ircland, M. G. Smith, J. Am. Chem. Soc. 1988, 110, 854-860.
34. B. E. Rossiter, T. R. Verhoeven, K. B. Sharpless, Tetrahedron Lett. 1979, 20, 4733-4736.
35. D. H. Barton, W. B. Motherwell, A. Stange, Synthesis 1981, 743-745.
36. The stereochemistry of the newly formed C12 stereocenter of tetrahydrofuran 20b was assigned by using 2D NMR spectroscopy.
37. J. W. Gillard, R. Fortin, H. E. Morton, C. Yoakim, C. A. Quesnelle, S. Daignault, Y. Guidan, J. Org. Chem. 1988, 53, 2602-2608.
38. This unusual protecting group offered the necessary acid stability during the synthesis, as well as the required fluoride ion lability for the final global deprotection with tris(dimethyamino)sulfur(trimethylsilyl) difluoride (See: K. A. Scheidt, H. Chen, B. C. Follows, S. R. Chemler, D. S. Coffey, W. R, Roush, J. Org. Chem. 1998, 63, 6436-6437). Under these conditions, the time required for C11-OTBS deprotection was prohibitively long. The use of a more base-labile TES ether did not afford the required acid stability during the synthesis.
39. S. V. Ley, L. R. Cox, J. Chem. Soc. Perkin Trans. 1 1997, 3315-3324.
40. 4] conveniently avoided any such side reactions.
41. 4] conveniently avoided any such side reactions.