2′-Methyl taxanes: Synthesis and NMR configurational assignment

Paolo Dambruoso; Carla Bassarello; Giuseppe Bifulco; Giovanni Appendino; Arturo Battaglia; Andrea Guerrini; Gabriele Fontana; Luigi Gomez-Paloma

doi:10.1016/j.tetlet.2005.03.095

2′-Methyl taxanes: Synthesis and NMR configurational assignment

Paolo Dambruoso
, Carla Bassarello
, Giuseppe Bifulco
, Giovanni Appendino
, Arturo Battaglia
, Andrea Guerrini
, Gabriele Fontana
, Luigi Gomez-Paloma

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	3411-3415
Number of pages	5
Journal	Tetrahedron Letters
Volume	46
Issue number	19
DOIs	https://doi.org/10.1016/j.tetlet.2005.03.095
Publication status	Published - 9 May 2005
Externally published	Yes

Keywords

J-Based configurational analysis
Relative configuration
Taxanes
Universal NMR Database

Access to Document

10.1016/j.tetlet.2005.03.095

Cite this

@article{d8e5fb7445ba4f3bbc0bad1695cb3488,

title = "2′-Methyl taxanes: Synthesis and NMR configurational assignment",

abstract = "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.",

keywords = "J-Based configurational analysis, Relative configuration, Taxanes, Universal NMR Database",

author = "Paolo Dambruoso and Carla Bassarello and Giuseppe Bifulco and Giovanni Appendino and Arturo Battaglia and Andrea Guerrini and Gabriele Fontana and Luigi Gomez-Paloma",

note = "Funding Information: The Universities of Salerno and Piemonte Orientale, MIUR (Roma), and Indena S.p.A. are gratefully acknowledged for financial support. The use of instrumental facilities of the Competence Center for Diagnostics and Molecular Pharmaceutics, sponsored by Regione Campania POR funds, is gratefully acknowledged. ",

year = "2005",

month = may,

day = "9",

doi = "10.1016/j.tetlet.2005.03.095",

language = "English",

volume = "46",

pages = "3411--3415",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "19",

}

TY - JOUR

T1 - 2′-Methyl taxanes

T2 - Synthesis and NMR configurational assignment

AU - Dambruoso, Paolo

AU - Bassarello, Carla

AU - Bifulco, Giuseppe

AU - Appendino, Giovanni

AU - Battaglia, Arturo

AU - Guerrini, Andrea

AU - Fontana, Gabriele

AU - Gomez-Paloma, Luigi

N1 - Funding Information: The Universities of Salerno and Piemonte Orientale, MIUR (Roma), and Indena S.p.A. are gratefully acknowledged for financial support. The use of instrumental facilities of the Competence Center for Diagnostics and Molecular Pharmaceutics, sponsored by Regione Campania POR funds, is gratefully acknowledged.

PY - 2005/5/9

Y1 - 2005/5/9

N2 - 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.

AB - 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.

KW - J-Based configurational analysis

KW - Relative configuration

KW - Taxanes

KW - Universal NMR Database

UR - https://www.scopus.com/pages/publications/17144399863

U2 - 10.1016/j.tetlet.2005.03.095

DO - 10.1016/j.tetlet.2005.03.095

M3 - Article

SN - 0040-4039

VL - 46

SP - 3411

EP - 3415

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 19

ER -

2′-Methyl taxanes: Synthesis and NMR configurational assignment

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this