Determination of the absolute configuration and total synthesis of radiosumin, a trypsin inhibitor from a freshwater blue-green alga

Tetrahedron Letters

Volumn 38, Issue 16, 1997, Pages 2883-2886

  Noguchi, Hirohide ^a   Aoyama, Toyohiko ^a   Shioiri, Takayuki ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

RADIOSUMIN; TRYPSIN INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030914059     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00488-7     Document Type: Article

References (15)

1. (a) Okino, R.; Matsuda, H.; Haraguchi, R.; Murakami, M.; Yamaguchi, K. 35th. Symposium on the Chemistry of Natural Products, Kyoto, Abstracts, 1993, 654.
2. (b) Matsuda, H.; Okino, T.; Murakami, M.; Yamaguchi, K. J. Org. Chem. 1996, 61, 8648.
3. Presented in part at the 34th Symposium on Peptide Chemistry held in Tsukuba on October 16-18; Peptide Chemistry 1996 (ed. by C. Kitada), Protein Research Foundation, Osaka, 1997, 6.
4. Presented in part at the 34th Symposium on Peptide Chemistry held in Tsukuba on October 16-18; Peptide Chemistry 1996 (ed. by C. Kitada), Protein Research Foundation, Osaka, 1997, 6.
5. Bicknell, A.J.; Burton, G.; Elder, J.S. Tetrahedron Lett. 1988, 29, 3361.
6. (a) Braun, H.; Felber, H.; Kresze, G.; Schmidtchen, F. P.; Prewo, R.; Vasella, A. Liebigs Ann. Chem. 1993, 261.
7. (b) Schürrle, K.; Beier, B.; Piepersberg, W. J. Chem. Soc. Perkin Trans. I 1991, 2407.
8. 1H NMR. The ratio of the other isomers was determined by HPLC analysis.
9. Corey, E. J.; Hopkins, P. B. Tetrahedron Lett. 1982, 23, 1979, and references cited therein.
10. Takuma, S.; Hamada, Y.; Shioiri, T. Chem. Pharm. Bull. 1982, 30, 3147 and references cited therein.
11. Hashimoto, N.; Aoyama, T.; Shioiri, T. Chem. Pharm. Bull. 1984, 32, 3759.
12. 3/MeOH=9:1). Retention time on HPLC of 18 and 19: 18a (9.5 min), 18b (12.4 min), 19a (16.2 min), and 19b (19.6 min) on DAICEL CHIRAL PAK AD; i-PrOH:hexane =1:2, UV(254 nm). The synthetic 18a was identical with the sample derived from natural radiosumin on HPLC analyses (DAICEL CHIRALCEL OD-H and YMC -Pack R&D R-SIL-5-06).
13. Salomon, C. J.; Mata, E. G.; Mascaretti, O. A. J. Chem. Soc. Perkin Trans, I 1996, 995, and references cited therein.
14. 2O) after retreatment with 8% aq. MeCN-0.05% TFA on HPLC.
15. The radiosumin methyl ester TFA salt was also obtained in 22% yield together with 41% recovery of the starting material 18a.