Synthesis of orthogonally protected lanthionines: A reassessment of the use of alanyl β-cation equivalents

Tetrahedron Letters

Volumn 43, Issue 46, 2002, Pages 8359-8362

  Mohd Mustapa, M Firouz ^a   Harris, Richard ^a   Mould, Jessica ^b   Chubb, Nathan A L ^b   Schultz, Darren ^b   Driscoll, Paul C ^a,c   Tabor, Alethea B ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

^c LUDWIG INSTITUTE FOR CANCER RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE DERIVATIVE; IODOALANINE; LANTHIONINE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037064506     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01981-0     Document Type: Article

References (16)

1. van Kraaij C., de Vos W.M., Siezen R.J., Kuipers O.P. Nat. Prod. Rep. 16:1999;575-587.
2. Ösapay G., Prokai L., Kim H.-S., Medzihradszky K.F., Coy D.H., Liapakis G., Reisine T., Melacini G., Zhu Q., Wang S.H.-H., Mattern R.-H., Goodman M. J. Med. Chem. 40:1997;2241-2251.
3. Polinsky A., Cooney M.G., Toy-Palmer A., Ösapay G., Goodman M. J. Med. Chem. 35:1992;4185-4194.
4. Melacini G., Zhu Q., Ösapay G., Goodman M. J. Med. Chem. 40:1997;2252-2258.
5. Alexander McNamara L.M., Andrews M.J.I., Mitzel F., Siligardi G., Tabor A.B. J. Org. Chem. 66:2001;4585-4594.
6. Harpp D.N., Gleason J.G. J. Org. Chem. 36:1971;73-79.
7. Cavelier-Frontin F., Daunis J., Jacquier R. Tetrahedron: Asymmetry. 3:1992;85-94.
8. Shao H., Wang S.H.H., Lee C.-W., Ösapay G., Goodman M. J. Org. Chem. 60:1995;2956-2957.
9. Probert J.M., Rennex D., Bradley M. Tetrahedron Lett. 37:1996;1101-1104.
10. Dugave C., Ménez A. Tetrahedron: Asymmetry. 8:1997;1453-1465.
11. Cherney R.J., Wang L. J. Org. Chem. 61:1996;2544-2546.
12. Barlos K., Papaicannou D., Theodoropoulos D. J. Org. Chem. 47:1982;1324-1326.
13. Kunz H., Waldmann H., Unverzagt C. Int. J. Pept. Prot. Res. 26:1985;493-497.
14. 6S requires C, 73.4; H, 6.3; N, 3.6; S, 4.2%.
15. 1H NMR.
16. The chemical shifts of each isomer of the two independently prepared diastereoisomers 11 and 7 are similar, but not identical. Previous work in which the two lanthionine diastereoisomers were unambiguously prepared have also shown the chemical shifts to be similar: Ösapay G., Zhu Q., Shao H., Chadha R.K., Goodman M. Int. J. Pept. Prot. Res. 46:1995;290-301.