Combined directed metalation-cross coupling strategies. Total synthesis of the aglycones of gilvocarcin V, M and E

Tetrahedron Letters

Volumn 38, Issue 47, 1997, Pages 8149-8152

  James, Clint A ^a   Snieckus, Victor ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; ANTINEOPLASTIC AGENT; GILVOCARCIN E; GILVOCARCIN M; GILVOCARCIN V; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONFORMATIONAL TRANSITION; CROSS REACTION; DRUG CONFORMATION; DRUG SYNTHESIS; STRUCTURE ACTIVITY RELATION;

LATEOLABRAX JAPONICUS;

EID: 0030683497     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10188-5     Document Type: Article

References (37)

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4. Knobler, R. M.; Radlwimmer, F. B.; Lane, M. J. Nucleic Acids Res. 1992, 20, 4553; Yamashita, Y.; Nakano, H. Nucleic Acids Res. Symp. Ser. 1988, 20, 65; Greenstein, M.; Monji, T.; Yeung, R. Maiese, W. M.; White, R. J. Antimicrob. Agents Chemother. 1986, 29, 861, and references cited therein.
5. Knobler, R. M.; Radlwimmer, F. B.; Lane, M. J. Nucleic Acids Res. 1992, 20, 4553; Yamashita, Y.; Nakano, H. Nucleic Acids Res. Symp. Ser. 1988, 20, 65; Greenstein, M.; Monji, T.; Yeung, R. Maiese, W. M.; White, R. J. Antimicrob. Agents Chemother. 1986, 29, 861, and references cited therein.
6. For literature concerning structural determination and an organized review of the synthetic work, see: a) Hua, D. H.; Saha, S. Recl. Trav. Chim. Pays-Bas 1995, 114, 341. Defucogilvocarcin V:
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21. Considerable effort was expended in the preparation of 6a, including the benzyne cycloaddition protocol of Suzuki (see Hosoya, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1994, 116, 1004 and references cited therein) which was abandoned due to a) inability to scale up the procedure, b) expense and limited availability of starting 2-methoxyfuran and c) modest yield (50%) in the cycloaddition step. An alternate method was adopted based on a modification of the selective reductive acylation of juglone derivatives by Giles (Chorn, T. A.; Giles, R. G. F.; Green, T. R.; Hugo, V. I.; Mitchell, P. R. K.; Yorke, S. C. J. Chem. Soc., Perkin Trans, I 1984, 1339).
22. Considerable effort was expended in the preparation of 6a, including the benzyne cycloaddition protocol of Suzuki (see Hosoya, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1994, 116, 1004 and references cited therein) which was abandoned due to a) inability to scale up the procedure, b) expense and limited availability of starting 2-methoxyfuran and c) modest yield (50%) in the cycloaddition step. An alternate method was adopted based on a modification of the selective reductive acylation of juglone derivatives by Giles (Chorn, T. A.; Giles, R. G. F.; Green, T. R.; Hugo, V. I.; Mitchell, P. R. K.; Yorke, S. C. J. Chem. Soc., Perkin Trans, I 1984, 1339).
23. +(67%).
24. a) Campi, E. M.; Jackson, W. R.; Marcuccio, S. M.; Naslund, C. G. M. J. Chem. Soc. Chem. Commun. 1984, 2395.
25. b) Suzuki, A. Pure Appl. Chem. 1994, 66, 213.
26. c) Campbell, M.G. Ph. D. Thesis, University of Waterloo, 1996.
27. In a model study on N.N-diethyl-2-(4-isopropoxy-3-methoxyphenyl)-l-naphthyl-O-carbamate, the migration/acid mediated cyclization protocol proceeded in 76% with no detectable cleavage of the isopropyl group.
28. In addition to 9a, decarbamoylated diisopropyl ether i and C-1 deisopropylated derivatives ii and iii were also isolated and characterized. These presumably result from LDA induced β-elimination assisted by C12 OMe coordination. For an analogous deisopropylation, see ref. 5b.
29. 2 showed no NOE. For a similar example of coordinative aryl ether cleavage, see Hua, D. H.; Saha, S.; Roche, D.; Maeng, J. C.; Iguchi, S.; Baldwin, C. J. Org. Chem. 1992, 57, 399.
30. +(72%).
31. Introduction of the base (2.5-3 equiv) in two portions separated by 1.5 h followed by cyclization gave 9b in 70% yld.
32. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
33. Merriman, G. H. Ph.D. Thesis, Ohio State University, Columbus, Ohio, 1990; Diss. Abstr. Int. B, 1991, 51, 5875, Order # 9111767.
34. Merriman, G. H. Ph.D. Thesis, Ohio State University, Columbus, Ohio, 1990; Diss. Abstr. Int. B, 1991, 51, 5875, Order # 9111767.
35. 3e
36. All new compounds show analytical and spectral data consistent with the depicted structures.
37. We are grateful to NSERC Canada and Monsanto/Searle for support under the Industrial Research Chair program.