Enantioselective total synthesis of antiangeogenic pentaketide dimers, epoxyquinols A and B, through an asymmetric aldol approach to their common monomeric precursor

Tetrahedron Letters

Volumn 46, Issue 4, 2005, Pages 547-549

  Kuwahara, Shigefumi ^a   Imada, Sunao ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Angeogenesis; Asymmetric aldol reaction; Epoxyquinol; Polyketide

Indexed keywords

ANGIOGENESIS INHIBITOR; DIMER; EPOXYQUINOL A; EPOXYQUINOL B; MONOMER; UNCLASSIFIED DRUG;

ALDOL REACTION; ANTIANGIOGENIC ACTIVITY; ARTICLE; DIMERIZATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; OXIDATION;

EID: 11144263601     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.001     Document Type: Article

References (24)

1. D.H. Paper Planta Med. 64 1998 686 695
2. C.J. Ryan, and G. Wilding Drugs Aging 17 2000 249 255
3. J. Folkman, T. Browder, and J. Palmblad Thromb. Haemostasis 86 2001 23 33
4. H. Kakeya, R. Onose, H. Koshino, A. Yoshida, K. Kobayashi, S.-I. Kageyama, and H. Osada J. Am. Chem. Soc. 124 2002 3496 3497
5. H. Kakeya, R. Onose, A. Yoshida, H. Koshino, and H. Osada J. Antibiot. 55 2002 829 831
6. M. Shoji, J. Yamaguchi, H. Kakeya, H. Osada, and Y. Hayashi Angew. Chem., Int. Ed. 41 2002 3192 3194
7. C. Li, S. Bardhan, E.A. Pace, M.-C. Liang, T.D. Gilmore, and J.A. Porco Jr. Org. Lett. 4 2002 3267 3270
8. M. Shoji, S. Kishida, M. Takeda, H. Kakeya, H. Osada, and Y. Hayashi Tetrahedron Lett. 43 2002 9155 9158
9. G. Mehta, and K. Islam Tetrahedron Lett. 44 2003 3569 3572
10. G. Mehta, and K. Islam Tetrahedron Lett. 45 2004 3611 3615
11. M. Shoji, S. Kishida, Y. Kodera, I. Shiina, H. Kakeya, H. Osada, and Y. Hayashi Tetrahedron Lett. 44 2003 7205 7207
12. H. Kakeya, Y. Miyake, M. Shoji, S. Kishida, Y. Hayashi, T. Kataoka, and H. Osada Bioorg. Med. Chem. Lett. 13 2003 3743 3746
13. M. Shoji, H. Imai, I. Shiina, H. Kakeya, H. Osada, and Y. Hayashi J. Org. Chem. 69 2004 1548 1556
14. For the biological activity of 4, see: Y. Miyake, H. Kakeya, T. Kataoka, and H. Osada J. Biol. Chem. 278 2003 11213 11220 See also Refs. 7,12
15. For a more practical synthesis of 1 and 2 via lipase-mediated kinetic resolution of a cyclohexenol intermediate, see Ref. 8
16. D.A. Evans, J. Bartroli, and T.L. Shih J. Am. Chem. Soc. 103 1981 2127 2129
17. M.T. Crimmins, and B.W. King J. Org. Chem. 61 1996 4192 4193
18. C. Börner, M.R. Dennis, E. Sinn, and S. Woodward Eur. J. Org. Chem. 2001 2435 2446
19. See, for example: P. Weyerstahl, H. Marschall, M. Weirauch, K. Thefeld, and H. Surburg Flavour Fragr. J. 13 1998 295 318
20. M. McNally, and R.J. Capon J. Nat. Prod. 64 2001 645 647
21. See, for example: M.T. Barros, C.D. Maycock, and M.R. Ventura J. Org. Chem. 62 1997 3984 3988
22. 3As in toluene at room temperature and the resulting mixture was heated at reflux, the reaction was very sluggish, resulting in only 21% yield of 12
23. M.F. Semmelhack, C.R. Schmid, D.A. Cortes, and C.S. Chou J. Am. Chem. Soc. 106 1984 3374 3376
24. 1H NMR spectrum suggested that the product might be another diastereomer of 1