Stereocontrolled synthesis of (+)-lycoperdic acid based on a palladium catalyzed reaction using a serine-derived organozinc reagent

Tetrahedron Letters

Volumn 41, Issue 24, 2000, Pages 4801-4804

  Masaki, Hidekazu ^a   Mizozoe, Tomoko ^a   Esumi, Tomoyuki ^a   Iwabuchi, Yoshiharu ^a   Hatakeyama, Susumi ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

Amino acids; Coupling reactions; Organozinc compounds; Palladium catalyzed reactions

Indexed keywords

AMINO ACID DERIVATIVE; DYSIHERBAINE; LYCOPERDIC ACID; NEUROTOXIN; ORGANOMETALLIC COMPOUND; PALLADIUM; SERINE DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

OXY;

EID: 0034660306     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00719-X     Document Type: Article

References (19)

1. Sakai, R.; Kamiya, H.; Murata, M.; Shimamoto, K. J. Am. Chem. Soc. 1997, 119, 4112-4116.
2. (a) Lamotte, J.; Oleksyn, B.; Dupont, L.; Dideberg, O.; Campsteyn, H.; Vermeire, M.; R-Banga, N. Acta Crystallogr. 1978, B34, 3635-3638.
3. (b) R-Banga, N.; Welter, A.; Jadot, J.; Casimir, J. Phytochemistry 1979, 18, 482-484.
4. For the synthesis of (+)-lycoperdic acid, see: (a) Kaname, M.; Yoshifuji, S. Tetrahedron Lett. 1992, 33, 8103-8104.
5. (b) Yoshifuji, S.; Kaname, M. Chem. Pharm. Bull. 1995, 43, 1617-1620.
6. (a) Jackson, R. F. W.; James, K.; Wythes, M. J.; Wood, A. J. Chem. Soc., Chem. Commun. 1989, 644-645.
7. (b) Jackson, R. F. W.; Wythes, M. J.; Wood, A. Tetrahedron Lett. 1989, 30, 5941-5944.
8. (c) Jackson, R. F. W.; Wishart, N.; Wood, A.; James, K.; Wythes, M. J. J. Org. Chem. 1992, 57, 3397-3404.
9. (d) Dunn, M. J.; Jackson, R. F. W.; Pietruszka, J.; Turner, D. J. Org. Chem. 1995, 60, 2210-2215.
10. Reviews: (a) Tamaru, Y. In Advances of Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: London, 1995; Vol. 4, pp. 41-72.
11. (b) Tamaru, Y. J. Synth. Org. Chem. Jpn. 1995, 53, 1102-1113.
12. For syntheses of amino acids using Jackson's methodology, see: (a) Ye, B.; Burke Jr., T. R. J. Org. Chem. 1995, 60, 2640-2641.
13. (b) Malan, C.; Morin, C. Synlett 1996, 167-168.
14. (c) Matsubara, J.; Otsubo, K.; Ohtani, S.; Kawano, Y.; Uchida, M. Heterocycles 1996, 43, 133-140.
15. (d) Torisawa, Y.; Soe, T.; Katoh, C.; Motohashi, Y.; Nishida, A.; Hino, T.; Nakagawa, M. Heterocycles 1998, 47, 655-659.
16. Denmark, S. E.; Jones, T. K. J. Org. Chem. 1982, 47, 4595-4597.
17. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Org. Chem. 1987, 109, 5765-5780.
18. Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.; Yonemitsu, O. Tetrahedron 1986, 42, 3021.
19. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.