Highly efficient ring closure of aromatic dialdehydes to macrocyclic allenes

Journal of the American Chemical Society

Volumn 119, Issue 15, 1997, Pages 3429-3433

  Brody, Marcus S ^a   Williams, Robin M ^a   Finn, M G ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; MACROCYCLIC COMPOUND;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; X RAY DIFFRACTION;

EID: 0030912650     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962868o     Document Type: Article

References (40)

1. Hughes, K. A.; Dopico, P. G.; Sabat, M.; Finn, M. G. Angew. Chem. Int., Ed. Engl. 1993, 32, 554-555.
2. Reynolds, K. A.; Dopico, P. G.; Sundermann, M. J.; Hughes, K. A.; Finn, M. G. J. Org. Chem. 1993, 58, 1298-1299.
3. Reynolds, K. A.; Dopico, P. G.; Brody, M. S.; Finn, M. G. J. Org. Chem. In press.
4. Reynolds, K. A.; Finn, M. G. J. Org. Chem. In press.
5. Stille, J. K.; Tanaka, M. J. Am. Chem. Soc. 1987, 109, 3785-3786.
6. Fujita, E. Pure Appl. Chem. 1981, 53, 1141-1154.
7. Nicolaou, K. C. Tetrahedron 1977, 33, 683-710.
8. Meng, Q.; Hesse, M. Topics in Current Chemistry: Ring Closure Methods in the Synthesis of Natural Products; Springer-Verlag: Berlin, 1991.
9. McQuillin, F. J.; Baird, M. S. Alicyclic Chemistry, 2nd ed.; Cambridge University Press: Cambridge, 1983.
10. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1994.
11. Lee, J. Y.; Kim, B. H. Tetrahedron 1996, 52, 571-588.
12. Sharma, A.; Sankaranarayanan, S.; Chattopadhyay, S. J. Org. Chem. 1996, 61, 1814-1816.
13. Rodgers, S. J.; Ng, C. Y.; Raymond, K. N. J. Am. Chem. Soc. 1985, 107, 4095-4096.
14. Schwartz, E.; Gottlieb, H. E.; Frolow, F.; Shanzer, A. J. Org. Chem. 1985, 50, 5469-5476.
15. Ma, S.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 6345-6357.
16. Stille, J. K.; Su, H.; Hill, D. H.; Schnieder, P.; Tanaka, M.; Morrison, D. L.; Hegedus, L. S. Organometallics 1991, 10, 1993-2000.
17. Johnson, E. P.; Chen, G.-P.; Fales, K. R.; Lenk, B. E.; Szendroi, R. J.; Wang, X.-J.; Carlson, J. A. J. Org. Chem. 1995, 60, 6595-6598.
18. Patterson, I.; Mansuri, M. M. Tetrahedron 1985, 41, 3569-3624.
19. Karin, M. R.; Sampson, P. J. Org. Chem. 1990, 55, 598-605.
20. McMurry, J. E. Acc. Chem. Res. 1983, 16, 405-411.
21. Becker, K. B. Tetrahedron 1980, 36, 1717-1745.
22. Nicolaou, K. C.; Seitz, S. P.; Pavia, M. R.; Petasis, N. A. J. Org. Chem. 1979, 44, 4011-4013.
23. Vollhardt, K. P. C. Synthesis 1975, 0, 765-780.
24. Schuster, H. F.; Coppola, G. M. Allenes in Organic Synthesis; John Wiley & Sons: New York, 1984.
25. Patai, S., Ed. The Chemistry of Ketenes, Allenes, and Related Compounds, Parts 1 and 2; Wiley-Interscience: Chichester, 1980.
26. Pasto, D. J. Tetrahedron 1984, 40, 2805-2827.
27. Marshall, J. A.; Wang, X. J. Org. Chem. 1992, 57, 3387-3396.
28. Okamura, W. H.; Aurrecoechea, J. M.; Gibbs, R. A.; Norman, A. W. J. Org. Chem. 1989, 54, 4072-4083.
29. 4
30. 2 present in the titanated ylide mixture. The resulting α-amino alkoxide adducts provide necessary basicity but remove those aldehyde equivalents from the olefination process. See ref 3 for a complete discussion.
31. For example, allene 3d is isolated in 75-85% yield if 2 equiv of 3,4,5-trimethoxybenzaldehyde are added to the Ti-substituted ylide mixture (1.41 mM), followed by 1.5 equiv of dialdehyde 2d. Allene 3c is obtained in 78% yield, 3e in 65% yield, and 9 in 49% yield (at room temperature) by this method. The choice of "blocking" monoaldehyde may be made to facilitate Chromatographic separation.
32. Koenig, K. E.; Lein, G. M.; Stuckler, P.; Kaneda, T.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 3553-3566.
33. 34,35 show a match between calculations of optical rotation of 1,3-diphenylallene and the lower of these two experimental values.
34. Ruch, E.; Runge, W.; Kresze, G. Angew. Chem., Int. Ed. Engl. 1973, 12, 20-25.
35. Runge, W.; Kresze, G. J. Am. Chem. Soc. 1977, 99, 5597-5603.
36. Geometry minimization was performed using the MM2 force field as implemented in Macromodel versions 4.0 and 4.5. Bond rotation about the binaphthyl C-C single bond was not constrained in the calculation, and so both diastereomers (composed of a single allene "epimer" and both possible binaphthyl structures) were evaluated in a single Monte Carlo conformational search of 15 000 starting structures, generating ten or more duplicates of the minimum-energy conformation of each diastereomer.
37. From the value obtained for the pure diastereomer, one would expect an optical rotation of approximately 166° for a 2.35:1 diastereomeric mixture, if the allene moiety was the sole contributor. A comparison with the observed value shows that the contribution of the binaphthyl fragment is of similar magnitude to the optical rotation of the binaphthyl dialdehyde precursor 8, as expected. Circular dichroism (THF, 5.78 μM) of the pure major diastereomer showed a negative Cotton effect, with extrema at 225 (Δε = 18.9 mdeg) and 237 nm (Δε = -22.8 mdeg), matching that of the binaphthyl aldehyde 8. The CD spectra of diarylallenes have been shown to strongly resemble those of binaphthyls in this frequency range [Mason, S. F.; Vane, G. W. Tetrahedron Lett. 1965, 1593-1597]. In addition, a region of negative Δε extends from 250 to 266 nm (Δε = ca. 5-8 mdeg) that is not exhibited by compound 8.
38. TEXSAN 5.0: Single Crystal Structure Analysis Software. Molecular Structure Corp.: The Woodlands, TX 77381, 1989.
39. teXsan 1.7: Single Crystal Sructure Analysis Software. Molecular Structure Corp.: The Woodlands, TX 77381, 1995.
40. Burla, M. C.; Camalli, M.; Cascarano, G.; Giacovazzo, C.; Polidori, G.; Spagna, R.; Viterbo, D. J. Appl. Crystallogr. 1989, 22, 389.