Erratum: Efficient solution phase parallel synthesis of norstatine analogs (Tetrahedron (2004) 60 (9043) DOI: 10.1016/j.tet.2004.07.085);Efficient solution phase parallel synthesis of norstatine analogs

Tetrahedron

Volumn 60, Issue 41, 2004, Pages 9043-9048

  Voronkov, Michael V ^a   Gontcharov, Alexander V ^b   Wang, Zhi Min ^c   Richardson, Paul F ^a   Kolb, Hartmuth C ^d  

^a LEXICON PHARMACEUTICALS INC   (United States)

^b WYETH RESEARCH   (United States)

^c Boston MA 02129 USA   (United States)

^d SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Epoxide; Nitrile; Norstatine; Solution phase combinatorial chemistry

Indexed keywords

GLYCIDOL; NITRILE; NORSTATINE DERIVATIVE; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; COMBINATORIAL CHEMISTRY; DERIVATIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 4444249327     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.10.045     Document Type: Erratum

References (18)

1. D.H. Rich, C.Q. Sun, J.V.N.V. Prasad, A. Pathiasseril, M.V. Toth, G.R. Marshall, M. Clare, R.A. Mueller, and K. Houseman J. Med. Chem. 34 1991 1222
2. T. Mimoto, J. Imai, S. Kisanuki, H. Enomoto, N. Hattori, K. Akaji, and Y. Kiso Chem. Pharm. Bull. 40 1992 2251
3. T.F. Tam, J. Carriere, I.D. MacDonald, A.L. Castelhano, D.H. Pliura, N.J. Dewdney, E.M. Thomas, C. Bach, J. Barnett, H. Chan, and A. Krantz J. Med. Chem. 35 1992 1318
4. J.J. Chen, P.J. Coles, L.D. Arnold, R.A. Smith, I.D. MacDonald, J. Carriere, and A. Krantz Bioorg. Med. Chem. Lett. 6 1996 435
5. G. Cardillo, A. Tolomelli, and C. Tomasini Eur. J. Org. Chem. 1999 155
6. E. Takashiro, I. Hayakawa, T. Nitta, A. Kasuya, S. Miyamoto, Y. Ozawa, R. Yagi, I. Yamamoto, T. Shibayama, A. Nakagawa, and Y. Yabe Bioorg. Med. Chem. 7 1999 2063
7. J.E. Semple, T.D. Owens, K. Nguyen, and O.E. Levy Org. Lett. 2 2000 2769
8. E.N. Zvonkova, A.S. Bushnev, N.E. Aksenov, N.K. Golovanova, and R.P. Evstigneeva J. Org. Chem. USSR 10 1974 1621
9. J. Legters, E. Van Dienst, L. Thijs, and B. Zwanenburg Recl. Trav. Chim. Pays-Bas 111 1992 69
10. J.L.G. Ruano, and C.G. Paredes Tetrahedron Lett. 41 2000 5357
11. D.J. Maly, L. Huang, and J.A. Ellman ChemBiochem 3 2002 16
12. A.R. Glabe, K.L. Sturgeon, S.B. Ghizzoni, W.K. Musker, and J.N. Takahashi J. Org. Chem. 61 1996 7212
13. Under various coupling conditions (resin-bound-DCC, PyBROP, etc.) LC/MS consistently indicated the corresponding (M-74) fragment, which corresponds to the formal loss of hydroxyacetic acid fragment, as a major component of the reaction mixture.
14. N.M. Weinshenker, and C.-M. Shen Tetrahedron Lett. 13 1972 3281
15. R.M. Lawrence, S.A. Biller, O.M. Fryszman, and M.A. Poss Synthesis 1997 553
16. Due to racemic nature of the amine moiety, the product was isolated as 1:1 mixture of diasteriomers.
17. N1 attack and results in multiple products.
18. Y. Gao, R.M. Hanson, J.M. Klunder, S.Y. Ko, H. Masamune, and K.B. Sharpless J. Am. Chem. Soc. 109 1987 5765