2′-Methyl taxanes:: Synthesis and NMR configurational assignment

被引：6

作者：

Dambruoso, P

Bassarello, C

Bifulco, G

Appendino, G

Battaglia, A

Guerrini, 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

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 19期

关键词：

taxanes; J-based configurational analysis; universal NMR database; relative configuration;

D O I：

10.1016/j.tetlet.2005.03.095

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Capitalizing on an oxidation-alkylation approach, a non-diastereoselective entry into 2'-methyl taxanes was developed. The issue of configurational assignment at the newly formed side-chain quaternary stereocenter was solved and put into a more general context by integrating information from, an alternative diastereoselective synthesis of model compounds and from spectroscopic measurements, critically comparing the J-Based and the Universal NMR Database approaches. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：3411 / 3415

页数：5

共 26 条

[1] (3R)-Chiral control of 3-alkyl-3-hydroxy-β-lactams via addition reaction of imines to enolates of 1,3-dioxolan-4-ones
Barbaro, G
Battaglia, A
Guerrini, A
Bertucci, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) : 4643 - 4651
[2] Stereochemical studies on ascaulitoxin:: a J-based NMR configurational analysis of a nitrogen substituted system
Bassarello, C
Bifulco, G
Evidente, A
Riccio, R
Gomez-Paloma, L
[J]. TETRAHEDRON LETTERS, 2001, 42 (49) : 8611 - 8613
[3] Synthesis of optically active constrained 2-substituted norstatines: A straightforward application of seebach's "SRS" synthetic principle
Battaglia, A
Guerrini, A
Bertucci, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (26) : 9055 - 9062
[4] Synthesis and biological evaluation of 2′-methyl taxoids derived from baccatin III and 14β-OH-baccatin III 1,14-carbonate
Battaglia, A
Bernacki, RJ
Bertucci, C
Bombardelli, E
Cimitan, S
Ferlini, C
Fontana, G
Guerrini, A
Riva, A
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (23) : 4822 - 4825
[5] Quantum mechanical calculations of NMR J coupling values in the determination of relative configuration in organic compounds
Bifulco, G
Bassarello, C
Riccio, R
Gomez-Paloma, L
[J]. ORGANIC LETTERS, 2004, 6 (06) : 1025 - 1028
[6] Advances in the universal NMR database approach.: 2′-substituted taxanes as probes for an improved protocol of diastereomeric differentiation
Dambruoso, P
Bassarello, C
Bifulco, G
Appendino, G
Battaglia, A
Fontana, G
Gomez-Paloma, L
[J]. ORGANIC LETTERS, 2005, 7 (06) : 983 - 986
[7] DOCETAXEL (TAXOTERE) DERIVATIVES - NOVEL NBCL3-BASED STEREOSELECTIVE APPROACH TO 2'-METHYLDOCETAXEL
DENIS, JN
FKYERAT, A
GIMBERT, Y
COUTTEREZ, C
MANTELLIER, P
JOST, S
GREENE, AE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (14): : 1811 - 1815
[8] The bioactive Taxol conformation on β-tubulin:: Experimental evidence from highly active constrained analogs
Ganesh, T
Guza, RC
Bane, S
Ravindra, R
Shanker, N
Lakdawala, AS
Snyder, JP
Kingston, DGI
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (27) : 10006 - 10011
[9] Diastereoselective addition of grignard reagents to azetidine-2,3-dione: Synthesis of novel Taxol(R) analogues
Kant, J
Schwartz, WS
Fairchild, C
Gao, Q
Huang, S
Long, BH
Kadow, JF
Langley, DR
Farina, V
Vyas, D
[J]. TETRAHEDRON LETTERS, 1996, 37 (36) : 6495 - 6498
[10] Kingston D G I, 2002, Fortschr Chem Org Naturst, V84, P53

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