Synthesis of the (9S,18R)-seco acid of the leukocyte adhesion inhibitor cyclamenol A

Tetrahedron Letters

Volumn 41, Issue 5, 2000, Pages 625-628

  Nazaré, Marc ^a   Waldmann, Herbert ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLAMENOL A; LACTAM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; LEUKOCYTE ADHERENCE INHIBITION;

EID: 0034728204     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02135-8     Document Type: Article

References (16)

1. T. A. Springer, Cell 1994, 76, 301-314.
2. Reviews: (a) Sears, P.; Wong, C.-H. Angew. Chem. 1999, 111, 2446-2471; Angew. Chem., Int. Ed. 1999, 38, 2300-2324;
3. Reviews: (a) Sears, P.; Wong, C.-H. Angew. Chem. 1999, 111, 2446-2471; Angew. Chem., Int. Ed. 1999, 38, 2300-2324;
4. (b) Giannis, A. Angew. Chem. 1994, 106, 188-191; Angew. Chem., Int. Ed. Engl. 1994, 33, 178-181.
5. (b) Giannis, A. Angew. Chem. 1994, 106, 188-191; Angew. Chem., Int. Ed. Engl. 1994, 33, 178-181.
6. Müller, H.; Bischoff, E.; Fiedler, V. B.; Weber, K.; Fugmann, B.; Rosen, B. Patent BAYER AG, DE 4231289 A1 940324.
7. Collum, D. B.; McDonald, J. H.; Still, W. C. J. Am. Chem. Soc. 1980, 102, 2118-2120.
8. Mueller, S.; Liepold, B.; Roth, G. J.; Bestmann, H. J. Synlett 1996, 521-522.
9. Durrant, G.; Green, R.; Lambeth, P.; Lester, M. G.; Taylor, N. R. J. Chem. Soc., Perkin. Trans. 1 1983, 2211-2214.
10. Zhang, H. Z.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857-1867.
11. Barrow, R.; Henscheidt, T.; Kieng, J.; Paik, S.; Moore, R. E.; Tius, M. A. J. Am. Chem. Soc. 1995, 117, 2479-2490.
12. Nicolaou, K. C.; Veale, C. A.; Webber, S. E.; Katerinopoulos, H. J. Am. Chem. Soc. 1985, 107, 7515-7518.
13. Sonagashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 50, 4467-4470.
14. Boland, W.; Schroer, N.; Sieler, C. Helv. Chim. Acta 1987, 70, 1025-1040.
15. 3), 3.05 (m, 1H, H′-19), 2.85 (m, 1H, H′-19), 2.40 (m, 2H, H-8), 2.20 (m, 1H, H-18), 1.02 (d, J=7.5 Hz, 3H, H-20).
16. Synthesis of (9S,18R)-cyclamenol A via a vanadium-mediated pinacol coupling as the key step: Nazaré, M.; Waldmann, H. Angew. Chem. 2000, 112, in press.