Advances in the universal NMR database approach.: 2′-substituted taxanes as probes for an improved protocol of diastereomeric differentiation

被引:5
作者
Dambruoso, P
Bassarello, C
Bifulco, G
Appendino, G
Battaglia, A
Fontana, G
Gomez-Paloma, L
机构
[1] Univ Piemonte Orientale, Fac Farm, DISCAFF, I-28100 Novara, Italy
[2] Univ Salerno, Fac Farm, Dipartimento Sci Farmaceut, I-84084 Fisciano, SA, Italy
[3] CNR, ISOF, Area Ric Bologna, I-40129 Bologna, Italy
[4] Indena SPA, I-20139 Milan, Italy
关键词
D O I
10.1021/ol047600d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The configuration of the alpha-substituted alpha-hydroxy-beta-aminoester moiety in a series of 2'-substituted taxanes was analyzed according to the recently proposed Universal NMR Database (UDB) approach. A critical analysis of the results showed that modifications regarding chemical shift adjustment (so as to render the shifts virtually connectivity independent) were necessary to get consistent stereoassignments in this set of compounds. On this basis, a modified UDB-based strategy, especially tailored to the configurational assignment of densely substituted diastereomeric fragments, is proposed.
引用
收藏
页码:983 / 986
页数:4
相关论文
共 18 条
  • [1] Barone G, 2002, CHEM-EUR J, V8, P3233, DOI 10.1002/1521-3765(20020715)8:14<3233::AID-CHEM3233>3.0.CO
  • [2] 2-0
  • [3] Barone G, 2002, CHEM-EUR J, V8, P3240, DOI 10.1002/1521-3765(20020715)8:14<3240::AID-CHEM3240>3.0.CO
  • [4] 2-G
  • [5] Generating diverse skeletons of small molecules combinatorially
    Burke, MD
    Berger, EM
    Schreiber, SL
    [J]. SCIENCE, 2003, 302 (5645) : 613 - 618
  • [6] DAMBRUOSO P, 2005, IN PRESS TETRAHEDRON
  • [7] Kobayashi Y, 2000, ANGEW CHEM INT EDIT, V39, P4279, DOI 10.1002/1521-3773(20001201)39:23<4279::AID-ANIE4279>3.0.CO
  • [8] 2-R
  • [9] Kobayashi Y, 2000, HELV CHIM ACTA, V83, P2562, DOI 10.1002/1522-2675(20000906)83:9<2562::AID-HLCA2562>3.0.CO
  • [10] 2-Z