Diastereoselective synthesis of all stereoisomers of β-methoxytyrosine, a component of papuamides

Journal of Organic Chemistry

Volumn 67, Issue 26, 2002, Pages 9210-9215

  Okamoto, Naoki ^a   Hara, Osamu ^a   Makino, Kazuishi ^a   Hamada, Yasumasa ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXIC ACTIVITIES; STEREOISOMERS;

CATALYST SELECTIVITY; SYNTHESIS (CHEMICAL);

ISOMERS;

CYCLODEPSIPEPTIDE; SERINE; TYROSINE DERIVATIVE;

ARTICLE; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; STEREOISOMERISM;

ANIMALS; ANTI-HIV AGENTS; ANTINEOPLASTIC AGENTS; COMBINATORIAL CHEMISTRY TECHNIQUES; DEPSIPEPTIDES; METHYLTYROSINES; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PAPUA NEW GUINEA; PEPTIDES, CYCLIC; PORIFERA; SERINE; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEREOISOMERISM;

EID: 0037184887     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0258352     Document Type: Article

References (24)

1. Ford, P. W.; Gustafson, K. R.; Mckee, T. C.; Shigematsu, N.; Maurizi, L. K.; Pannell, L. K.; Williams, D. E.; Silva, E. D.; Lassota, P.; Allen, T. M.; Soest, R. V.; Anderson, R. J.; Boyd, M. R. J. Am. Chem. Soc. 1999, 121, 5899-5905.
2. Zampella, A.; D'Auria, M. V.; Paloma, L. G.; Casapullo, A.; Minale, L.; Debitus, C.; Henin, Y. J. Am. Chem. Soc. 1996, 118, 6202-6209.
3. Liang, B.; Carroll, P. J.; Joullie, M. M. Org. Lett. 2000, 2, 4157-4160.
4. Okamoto, N.; Hara, O.; Makino, K.; Hamada, Y. Tetrahedron: Asymmetry 2001, 12, 1353-1358.
5. Makino, K.; Okamoto, N.; Hara, O.; Hamada, Y. Tetrahedron: Asymmetry 2001, 12, 1757-1762.
6. (a) Shimamoto, K.; Ohfune, Y. Tetrahedron Lett. 1988, 29, 5177-5180.
7. (b) Easton, C. J.; Hutton, C. A.; Tan, E. W.; Tiekink, E. R. T. Tetrahedron Lett. 1990, 31, 7059-7062.
8. (c) Blaser, D.; Seebach, D. Liebigs Ann. Chem. 1991, 1067-1078.
9. (d) Easton, C. J.; Hutton, C. A.; Roselt, P. D.; Tiekink, E. R. T. Tetrahedron 1994, 50, 7327-7340.
10. (a) Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979-2984.
11. (b) Garner, P.; Park, J. M. Org. Synth. 1992, 70, 18.
12. Williams, L.; Zhang, Z.; Shao, F.; Carrol, P. J.; Joullie, M. M. Tetrahedron 1996, 52, 11673-11694.
13. (a) Herold, P. Helv. Chim. Acta 1988, 71, 354-362.
14. (b) Nimkar, S.; Menaldino, D.; Merrill, A. H.; Liotta, D. Tetrahedron Lett. 1988, 29, 3037-3040.
15. (c) Garner, P.; Park, J. M.; Malecki, E. J. Org. Chem. 1988, 53, 4395-4398.
16. (d) Radunz, H. E.; Devant, R. M.; Eiermann, V. Liebigs. Ann. Chem. 1988, 1103-1105.
17. Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439-1446.
18. Peng, S.; Qing, F. L. J. Chem. Soc., Perkin Trans. 1 1999, 3345-3348.
19. Kitagawa, K.; Inoue, A.; Shinokubo, H.; Ohshima, K. Angew. Chem., Int. Ed. 2000, 39, 2481-2483.
20. 1H NMR and HPLC analysis using Chiralcel OD-H.
21. Nishida, A.; Sorimachi, H.; Iwaida, M.; Matsumizu, M.; Kawate, T.; Nakagawa, M. Synlett 1998, 389-390.
22. Hamada, Y.; Shioiri, T. Chem. Pharm. Bull. 1982, 30, 1921- 1924.
23. The enantiomeric purity of 9 was measured by HPLC analysis using a chiral column (Daicel Chiralcel OJ, 25 cm; 10% i-PrOH in n-hexane; flow rate = 0.5 mL/min; -9, 41.8 min; -9, 35.7 min) and found to be S (>99% ee).
24. The opitical purity of (2R,3R)-4 was confirmed by HPLC analysis of the corresponding methyl ester using a chiral column (Daicel Chiralcel OD-H.; 10% i-PrOH in n-hexane; flow rate = 0.5 mL/ min; (2R,3R)-4, 10.4 min; (2S,3S)-4, 12.4 min).