Studies on synthesis of optically active twelve-membered diynes: A convergent construction of a twelve-membered diketodiyne compound with C2 symmetry

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 5, 2000, Pages 737-744

  Mukai, Chisato ^a   Kasamatsu, Eiji ^a   Ohyama, Takao ^a   Hanaoka, Miyoji ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; DERIVATIVES; IODINE; REACTION KINETICS; SYNTHESIS (CHEMICAL);

COUPLING REACTION;

AROMATIC COMPOUNDS;

EID: 0034615523     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/a909089d     Document Type: Article

References (42)

1. N. Ishida. K. Miyazaki, K. Kumagai and M. Rikimaru, J. Antibiot., 1965, 18, 68.
2. K. Edo, M. Mizugaki, Y. Koide, H. Seto, K. Furihata, N. Otakd and N. Ishida, Tetrahedron Lett., 1985, 26, 331.
3. K. S. Lam, G. A. Hesler, D. R. Gustavson, A. R. Crosswell, J. M. Veitch, S. Forenza and K. Tomita, J. Antibiot., 1991, 44, 472.
4. J. Hu, Y.-C. Xue, M.-Y. Xie, Y. Zhang, T. Otani, Y. Minami, Y. Yamada and T. Marunaka, J. Antibiot., 1988, 41, 1575.
5. M. Hanada, H. Ohkuma, T. Yonemoto, K. Tomita, M. Ohbayashi, H. Kamei, T. Miyaki, M. Konishi, H. Kawaguchi and S. Forenza, J. Antibiot., 1991, 44, 403.
6. T. Ando, M. Ishii, T. Kajiura, Y. Kameyama, K. Miwa and Y. Sugiura, Tetrahedron Lett., 1998, 39, 6495.
7. (a) P. A. Wender, M. Harmata, D. Jeffrey, C. Mukai and J. Suffert, Tetrahedron Lett., 1988, 29, 909;
8. (b) P. A. Wender, J. A. McKinney and C. Mukai, J. Am. Chem. Soc., 1990, 112, 5369;
9. (c) P. Magnus and M. Davis, J. Chem. Soc., Chem. Comnnm., 1991, 1522;
10. (d) T. Takahashi, H. Tanaka, Y. Hirai, T. Doi, H. Yamada, T. Shiraki and Y. Sugiura, Angew. Chem., Int. Ed. Engl., 1993, 32, 1657;
11. (e) A. G. Myers, M. Hammond, Y. Wu, J.-N. Xiang, P. M. Harrington and E. Y. Kuo, J. Am. Client. Soc., 1996, 118, 10006;
12. (f) P. Magnus, R. Carter, M. Davis, J. Elliott and T. Pitterna, Tetrahedron Lett., 1996, 37, 6283;
13. (g) S. Caddick and V. M. Delisser, Tetrahedron Lett., 1997, 38, 2355.
14. (a) M. Hirama, K. Fujiwara, K. Shigematu and Y. Fukazawa, J. Am. Chem. Soc., 1989, 111, 4120;
15. (b) M. Hirama, T. Gomibuchi and K. Fujiwara, J. Am. Chem. Soc., 1991, 113, 9851;
16. (c) K. Nakatani, K. Aral and S. Terashima, J. Chem. Soc., Chem. Commun., 1992, 289;
17. (d) J. Suffert, E. Abraham, S. Raeppel and R. Brückner, Liebigs Ann. Chem., 1996, 334;
18. (e) K. Brickmann, F. Hambloch, J. Suffert and R. Brückner, Liebigs Ann. Chem., 1996, 357;
19. (f) M. Eckhardt and R. Bruckner, Liebigs Ann. Chem., 1996, 473 and references cited therein.
20. During this investigation, Myers and Goldberg have recently reported a novel transformation reaction of the twelve-membered tetrayne derivative into the corresponding bicyclo[7.3.0]dodecadienediyne: A. G. Myers and S. D. Goldberg, Tetrahedron Lett., 1998, 39, 9633.
21. For recent reviews on medium-sized cyclic diynes, see (a) R. Gleiter and R. Merger, in Cyclic Alkynes, Preparation and Properties in Modern Acetylene Chemistry, ed. P. J. Stang and F. Diederich, VCH, Weinheim, 1995, p. 285;
22. (b) C. Boss and R. Keese, Tetrahedron, 1997, 53, 3111 and references cited therein.
23. J. Kuszmann, Carbohydr. Res., 1979, 71, 123.
24. M. Yamaguchi and I. Hirao, Tetrahedron Lett., 1983, 24, 391.
25. B. B. Lohray, Y. Jayamma and M. Chatterjee, J. Org. Chem., 1995, 60, 5958.
26. J. E. Baldwin, J. Chem. Soc., Chem. Commun., 1976, 734.
27. H. Nemoto, S. Takamatsu and Y. Yamamoto, J. Org. Chem., 1991, 56, 1321.
28. E. J. Corey and P. L. Fuchs, Tetrahedron Lett., 1972, 13, 3769.
29. Y. L. Merrer, A. Dureault, C. Greek, D. M. Languin, C. Gravier and J.-C. Depezay, Heterocycles, 1987, 25, 541.
30. Numbering for NCS chromophore (1) was employed for convenience.
31. 13C NMR spectrum. 20 A similar isomerization from the propargyl (prop-2-ynyl) ketone moiety to the corresponding allenyl ketone functionality was reported: (a) G. Majetich, Y. Zhang and G. Dreyer, Tetrahedron Lett., 1993, 34, 449;
32. (b) A. S. K. Hashmi, J. W. Bats, J.-H. Choi and L. Schwarz, Tetrahedron Lett., 1998, 39, 7491 and references cited therein.
33. A. C. Cope and A. S. Mehta, J. Am. Chem. Soc., 1964, 86, 5626.
34. (a) A. G. Myers, P. M. Harrington and E. Y. Kuo, J. Am. Chem. Soc., 1991, 113, 694;
35. (b) K. Iida and M. Hirama, J. Am. Chem. Soc., 1994, 116, 10310;
36. (c) I. Sato, K. Toyama, T. Kikuchi and M. Hirama, Synlett, 1998, 1308.
37. (a) K. C. Nicolaou, A. Liu, Z. Zeng and S. McComb, J. Am. Chem. Soc., 1992, 114, 9279;
38. (b) C. Meert, J. Wane and P. J. De Clercq, Tetrahedron Lett., 1997, 38, 2179;
39. (c) M. F. Semmelhack, Y. Gu and D. M. Ho, Tetrahedron Lett., 1997, 38, 5583.
40. T. Nishizawa, S. Shibuya, S. Hosokawa and M. Isobe, Synlett, 1994, 485.
41. Several attempts were made to develop a more convenient procedure involving fewer steps for obtaining 34. For example, the dialdehyde compound derived from 26 (e.g., compound 6 in Scheme 1) was reacted with dicerium acetylide or diiodoacetylene derivatives, prepared from 13, to afford an intractable mixture.
42. Several preliminary attempts on conversion of 35 into the corresponding bicyclo[7.3.0]dodecadiyne derivatives were made under typical aldol conditions by using LDA or LHMDS. However, no ring closed compounds have so far been isolated from the reaction mixture.