Synthetic studies on tetrazomine: Stereochemical assignment of the β- hydroxypipecolic acid

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3659-3662

  Scott, Jack D ^a   Tippie, Tracy N ^a   Williams, Robert M ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; PIPECOLIC ACID;

ANTIMICROBIAL ACTIVITY; ARTICLE; DNA CLEAVAGE; DRUG ISOLATION; DRUG SYNTHESIS; GENE ASSIGNMENT; HYDROLYSIS; NONHUMAN; PROTEIN DNA INTERACTION; STEREOCHEMISTRY;

EID: 0032575194     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00642-X     Document Type: Article

References (19)

1. 1. (a) Sato, T.; Hirayama, F.; Saito, T., J. Antibiotics 1991, 44, 1367-1370;
2. (b) Suzuki, K., et al., J. Antibiot. 1991, 44, 479-485.
3. 2. (a) Williams, R.M.; Flanagan, M.E.; Tippie, T., Biochemistry 1994, 33, 4086-4092;
4. (b) Flanagan, M.E.; Rollins, S.B.; Williams, R.M., Chemistry and Biology 1995, 2, 147-156.
5. 3. Flanagan, M.E., Williams, R.M., J. Org. Chem. 1995, 60, 6791-6797.
6. 4. Knight, D.W.; Lewis, N.; Share, A.C.; Haigh, D., Tetrahedron Asymmetry 1993, 4, 625-628. This paper does not describe the synthesis of the free amino acid but the protected version: N-t-BOC (2R, 3S)-3-hydroxymethyl pipecolate which has been converted to 3a (this work, ref. 11).
7. 5. (a) Roemmele, R.C.; Rapoport, H., J. Org. Chem. 1989, 54, 1866-1875;
8. (b) for a synthesis of the racemic synisomer, see: Makara, G.; Marshall, G.R., Tetrahedron Lett. 1997, 38, 5069-5072.
9. 6. For other syntheses of the anti-isomers (2a and 2b), see: (a) Greek, C.; Ferreira, F.; Genet, J.P., Tetrahedron Lett. 1996, 37, 2031-2034;
10. (b) Ferreira, F.; Greck, C.; Genet, J.P., Bull. Soc. Chim. Fr. 1997, 134, 615-621;
11. (c) Battistini, L.; Zanardi, F.; Rassu, G.; Spanu, P.; Pelosi, G.; Fava, G.G.; Ferrari, M.B.; Casiraghi, G., Tetrahedron Asymmetry 1997, 8, 2975-2987;
12. (d) Agami, C.; Couty, F.; Mathieu, H., Tetrahedron Lett. 1996, 37, 4001-4002.
13. 7. For general experimental procedures for carrying out the boron enolate aldolization, see: Williams, R.M.; Yuan, C., J. Org. Chem. 1992, 57, 6519-6527.
14. 3).
15. 20 = - 3.7 (c = 1.25, CHCl3).
16. 3).
17. 4 on a Waters 600 HPLC with a UV detector at 210 nm).
18. 2 followed by removal of the solvent and treatment of the amino methyl ester with KOH in water at room temperature. Acidic Dowex-50WX2-100 ion exchange resin treatment (eluted within 2% ammonium hydroxide) afforded the free amino acid 3a (81% for two steps). To our knowledge, physical data for the free amino acid (3a) have not been previously reported.
19. 20 = +82.1° (c=0.12, 1M HCl).