Anna M. Costa

Universitat de Barcelona

Author Statistics

Papers

Citation

H-Index

i-10 index

Research Trends

Author Order

Document Type

Co-Authors

Jaume Vilarrasa

Universitat de Barcelona

Fèlix Urpı́

Universitat de Barcelona

Lluís Bosch

Universitat Autònoma de Barcelona

Stuart C. D. Kennington

Universitat de Barcelona

Pedro Romea

Universitat de Barcelona

Alejandro Castro‐Alvarez

Universidad de La Frontera

Elena Petit

Universitat de Barcelona

Pere M. Deyà

Universitat de les Illes Balears

Gabriel Aullón

Universitat de Barcelona

Mercè Font‐Bardía

Universitat de Barcelona

Cooperative Institutions

Universitat de Barcelona

Neurological Surgery

FC Barcelona

The University of Tokyo

Institut de Biomedicina de la Universitat de Barcelona

Universitat de les Illes Balears

Centre National de la Recherche Scientifique

Consejo Superior de Investigaciones Científicas

Inserm

University of Toronto

Author Statistics

Papers

Citation

H-Index

i-10 index

Research Field

Temperature‐dependent nonlinear effects and catalyst evolution in the asymmetric addition of diethylzinc to benzaldehyde

Israel Journal of Chemistry (2001)

Jaume Balsells Anna M. Costa Patrick J. Walsh

Abstract Several efficient and highly enantioselective titanium‐based catalysts promote the asymmetric addition of alkyl groups to aldehydes. The catalysts involved in these reactions have been found not to exhibit nonlinear behavior. We have been able to identify a series of chiral bis(sulfonamide)‐based titanium catalysts that do show nonlinear behavior. Monitoring of the product ee's (ee p 's) at different conversions and different temperatures has led us to propose that nonlinear behavior is caused by an autoinduction process rather than by catalyst aggregation. Evidence to support this hypothesis includes ee p 's that change with the extent of conversion. We have found that when enantiopure ligand was used, the ee p increases with conversion from 72% to 80%. However, use of non‐enantiopure ligand results in ee p 's that decrease with conversion. These results are rationalized by different rates of alkoxide exchange processes between like and unlike titanium‐alkoxide containing complexes.

Enantiopure drug

Diethylzinc

Alkoxide

Benzaldehyde

10.1560/lm1c-rrq5-12aj-njjc

Cite

Citations (12)

CCDC 2190990: Experimental Crystal Structure Determination

The Cambridge Structural Database (2023)

Miguel Mellado‐Hidalgo Elias A. Romero-Cavagnaro Sajanthanaa Nageswaran Sabrina Puddu Stuart C. D. Kennington

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc2cjx3y

Cite

Citations (0)

Synthesis of Amphidinolide E C10−C26 Fragment

Organic Letters (2008)

Jorge Martín Esteban Anna M. Costa Jaume Vilarrasa

The key C10-C26 fragment in a total synthesis of (-)-amphidinolide E has been prepared from an oxolane-containing C10-C17 segment (9, derived from L-glutamic acid) via a Julia-Kocienski reaction with aldehyde 3, followed by a Sharpless AD to obtain the desired diol. The C22-C26 fragment was installed by means of an efficient Suzuki-Molander coupling, with an organotrifluoroborate reagent (4, arising from a cross-metathesis reaction between a vinylboronate and 2-methyl-1,4-pentadiene).

Fragment (logic)

10.1021/ol801923y

Cite

Citations (17)

Synthesis of Lapachol Analogues through Suzuki-Miyaura Cross-Coupling. Antitumoral Evaluation.

Proceedings of the 15th Brazilian Meeting on Organic Synthesis Proceedings (2013)

Sara L. S. Gomes Anna M. Costa Gardênia Carmen Gadelha Militão Paulo R. R. Costa A. J. M. da Silva

Lapachol (Figure 1) is a naphtoquinone extracted from the bark of Pau d`Arco. This compound presents antineoplasic activity that is associated to the DNA repair inhibition and also acts as an oxidation and phosphorylation inhibitor in the mitochondria. It is believed that the presence of the prenyl group is important to the observed activity. Recently, the molluscicidal, antimalarial, antitrypanosomal and antiviral activities of lapachol and analogues have been reported.

10.5151/chempro-14bmos-r0034-1

Cite

Citations (0)

The Performance of Several Docking Programs at Reproducing Protein–Macrolide-Like Crystal Structures

Molecules (2017)

Alejandro Castro‐Alvarez Anna M. Costa Jaume Vilarrasa

The accuracy of five docking programs at reproducing crystallographic structures of complexes of 8 macrolides and 12 related macrocyclic structures, all with their corresponding receptors, was evaluated. Self-docking calculations indicated excellent performance in all cases (mean RMSD values ≤ 1.0) and confirmed the speed of AutoDock Vina. Afterwards, the lowest-energy conformer of each molecule and all the conformers lying 0-10 kcal/mol above it (as given by Macrocycle, from MacroModel 10.0) were subjected to standard docking calculations. While each docking method has its own merits, the observed speed of the programs was as follows: Glide 6.6 > AutoDock Vina 1.1.2 > DOCK 6.5 >> AutoDock 4.2.6 > AutoDock 3.0.5. For most of the complexes, the five methods predicted quite correct poses of ligands at the binding sites, but the lower RMSD values for the poses of highest affinity were in the order: Glide 6.6 ≈ AutoDock Vina ≈ DOCK 6.5 > AutoDock 4.2.6 >> AutoDock 3.0.5. By choosing the poses closest to the crystal structure the order was: AutoDock Vina > Glide 6.6 ≈ DOCK 6.5 ≥ AutoDock 4.2.6 >> AutoDock 3.0.5. Re-scoring (AutoDock 4.2.6//AutoDock Vina, Amber Score and MM-GBSA) improved the agreement between the calculated and experimental data. For all intents and purposes, these three methods are equally reliable.

Docking (animal)

10.3390/molecules22010136

Cite

Citations (168)

A Formal Total Synthesis of Eleutherobin Through an Unprecedented Kinetically Controlled Ring‐Closing‐Metathesis Reaction of a Densely Functionalized Diene

Angewandte Chemie International Edition (2004)

Damiano Castoldi Lorenzo Caggiano Laura Panigada Ofer Sharon Anna M. Costa

The key step in a formal total synthesis of eleutherobin was an unprecedented kinetically controlled RCM reaction of a densely functionalized diene 1 bearing two PMP-protected allylic alcohols in the presence of a second-generation Grubbs catalyst. Subsequent isomerization of the E 10-membered enedione 2 to the more stable Z isomer and cleavage of the MOM protecting group led to the known precursor 3. MOM=methoxymethyl; PMP=p-methoxyphenyl.

Diene

Ring-Closing Metathesis

Salt metathesis reaction

Cleavage (geology)

10.1002/anie.200461767

Cite

Citations (48)

Substrate Dependence of Nonlinear Effects: Mechanistic Probe and Practical Applications

Journal of the American Chemical Society (2001)

Young K. Chen Anna M. Costa Patrick J. Walsh

ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTSubstrate Dependence of Nonlinear Effects: Mechanistic Probe and Practical ApplicationsYoung K. Chen, Anna M. Costa, and Patrick J. WalshView Author Information P. Roy and Diane T. Vagelos Laboratories Department of Chemistry, University of Pennsylvania 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323 Cite this: J. Am. Chem. Soc. 2001, 123, 22, 5378–5379Publication Date (Web):May 10, 2001Publication History Received12 March 2001Revised24 April 2001Published online10 May 2001Published inissue 1 June 2001https://pubs.acs.org/doi/10.1021/ja0158004https://doi.org/10.1021/ja0158004rapid-communicationACS PublicationsCopyright © 2001 American Chemical SocietyRequest reuse permissionsArticle Views732Altmetric-Citations33LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-AlertscloseSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Aldehydes,Catalysts,Chemical reactions,Ligands,Oligomers Get e-Alerts

10.1021/ja0158004

Cite

Citations (36)

Amphidinolides and Iriomoteolides, Potent Anticancer Macrolides

Lluís Bosch Víctor Cascales Alejandro Castro‐Alvarez C Inserra Marco Elena Petit

Open AccessExtended Abstract Amphidinolides and Iriomoteolides, Potent Anticancer Macrolides † by Lluís Bosch, Víctor Cascales, Alejandro Castro-Alvarez, Cristian Marco, Elena Petit, Anna M. Costa * and Jaume Vilarrasa Secció de Química Orgànica, Facultat de Química, Universitat de Barcelona, 08028 Barcelona, Spain * Author to whom correspondence should be addressed. † Presented at the 2nd Molecules Medicinal Chemistry Symposium (MMCS): Facing Novel Challenges in Drug Discovery, Barcelona, Spain, 15–17 May 2019. Proceedings 2019, 22(1), 41; https://doi.org/10.3390/proceedings2019022041 Published: 8 August 2019 (This article belongs to the Proceedings of The 2nd Molecules Medicinal Chemistry Symposium (MMCS): Facing Novel Challenges in Drug Discovery) Download PDF Citation Export BibTeX EndNote RIS Cite This Paper

Anticancer drug

10.3390/proceedings2019022041

Cite

Citations (0)

CCDC 645873: Experimental Crystal Structure Determination

The Cambridge Structural Database (2008)

Carmen Rotger Bartolomé Soberats David Quiñonero Antonio Frontera Pablo Ballester

10.5517/ccpp2m1

Cite

Citations (0)

Michael Addition−Elimination Reactions of Chiral Enolates with Ethyl 3-Halopropenoates

Organic Letters (2007)

Jorge Martín Esteban Anna M. Costa Alex Joffre Quimis Gómez Jaume Vilarrasa

Key dienoic or dienal substructures of cytotoxic macrolides amphidinolide E and dictyostatin have been prepared via a Michael addition (followed by elimination of X-) of chiral enolates on beta-halo derivatives of ethyl acrylate, with full retention of the initial E or Z configuration. Evans oxazolidin-2-ones and our related thiazolidin-2-ones, as well as a fine-tuning of the reaction conditions, have been essential. Many chiral building blocks are accessible from these adducts.

Michael reaction

Addition reaction

Ethyl acrylate

Elimination reaction

10.1021/ol702632m

Cite

Citations (30)