Table of Contents

May 11, 2007
Volume 72, Issue 10
Pages 3609-3980

About the Cover: Just as children use blocks to engineer structures and compose words, medicinal chemists use functional groups to build molecules that evoke biological responses. Using combinatorial chemistry in conjunction with rational drug design, small molecule inhibitors of the Hsp90 protein folding machinery have been prepared based on the natural product, novobiocin. See Blagg and Huang, p 3609. View the article.

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Articles

A Library of Noviosylated Coumarin Analogues

Yung-Tzung Huang and Brian S. J. Blagg
pp 3609–3613
Publication Date (Web): March 01, 2007 (Article)
DOI: 10.1021/jo062083t

Synthesis and Binding Studies of Alzheimer Ligands on Solid Support

Petra Rzepecki, Nina Geib, Manuel Peifer, Frank Biesemeier, and Thomas Schrader
pp 3614–3624
Publication Date (Web): April 12, 2007 (Article)
DOI: 10.1021/jo061918x

Methylation of Sydnone N-Oxides:  Kinetic and Thermodynamic Control in the Alkylation Site of an Electron-Rich Heterocycle

D. Scott Bohle, Lindsey E. McQuade, Inna Perepichka, and Lijuan Zhang
pp 3625–3631
Publication Date (Web): April 18, 2007 (Article)
DOI: 10.1021/jo062235k

Synthesis, Spectroscopic, Electrochemical and Pb2+-Binding Studies of Tetrathiafulvalene Acetylene Derivatives

Yao-Peng Zhao, Li-Zhu Wu, Gang Si, Yan Liu, Hai Xue, Li-Ping Zhang, and Chen-Ho Tung
pp 3632–3639
Publication Date (Web): April 19, 2007 (Article)
DOI: 10.1021/jo0622577

Cyclodextrin-Driven Movement of Cucurbit[7]uril

Yu Liu, Xiao-Yun Li, Heng-Yi Zhang, Chun-Ju Li, and Fei Ding
pp 3640–3645
Publication Date (Web): February 20, 2007 (Article)
DOI: 10.1021/jo0624288

Electrosynthesis of Symmetric and Highly Conjugated Benzofuran via a Unique ECECCC Electrochemical Mechanism:  Evidence for Predominance of Electrochemical Oxidation versus Intramolecular Cyclization

Davood Nematollahi, Amene Amani, and Esmail Tammari
pp 3646–3651
Publication Date (Web): April 10, 2007 (Article)
DOI: 10.1021/jo062468b

Synthesis and Photovoltaic Properties of Efficient Organic Dyes Containing the Benzo[b]furan Moiety for Solar Cells

Il Jung, Jae Kwan Lee, Kyu Ho Song, Kihyung Song, Sang Ook Kang, and Jaejung Ko
pp 3652–3658
Publication Date (Web): March 30, 2007 (Article)
DOI: 10.1021/jo0625150

Independent Generation of C5‘-Nucleosidyl Radicals in Thymidine and 2‘-Deoxyguanosine

Antonio Manetto, Dimitris Georganakis, Leondios Leondiadis, Thanasis Gimisis, Peter Mayer, Thomas Carell, and Chryssostomos Chatgilialoglu
pp 3659–3666
Publication Date (Web): April 11, 2007 (Article)
DOI: 10.1021/jo062518c

Synthesis of Dimethyl Gloiosiphone A by Way of Palladium-Catalyzed Domino Cyclization

Takayuki Doi, Yusuke Iijima, Masaru Takasaki, and Takashi Takahashi
pp 3667–3671
Publication Date (Web): April 12, 2007 (Article)
DOI: 10.1021/jo062546v

Oxidation of 2‘-Deoxycytidine to Four Interconverting Diastereomers of N1-Carbamoyl-4,5-dihydroxy-2-oxoimidazolidine Nucleosides

Sébastien Tremblay, Tsvetan Gantchev, Luc Tremblay, Pierre Lavigne, Jean Cadet, and J. Richard Wagner
pp 3672–3678
Publication Date (Web): April 18, 2007 (Article)
DOI: 10.1021/jo062386n

Nucleophilicities of Primary and Secondary Amines in Water

Frank Brotzel, Ying Cheung Chu, and Herbert Mayr
pp 3679–3688
Publication Date (Web): April 06, 2007 (Article)
DOI: 10.1021/jo062586z

The Synthesis and Inhibitory Activity of Dethiotrypanothione and Analogues against Trypanothione Reductase

Josephine A. Czechowicz, April K. Wilhelm, Maroya D. Spalding, Anna M. Larson, Linnea K. Engel, and David G. Alberg
pp 3689–3693
Publication Date (Web): April 17, 2007 (Article)
DOI: 10.1021/jo062597s

Efficient Synthesis of β-d-Mannosides and β-d-Talosides by Double Parallel or Double Serial Inversion

Hai Dong, Zhichao Pei, Marcus Angelin, Styrbjörn Byström, and Olof Ramström
pp 3694–3701
Publication Date (Web): April 18, 2007 (Article)
DOI: 10.1021/jo062643o

Studies on the Intramolecular Cyclizations of Bicyclic δ-Hydroxynitriles Promoted by Triflic Anhydride

Valeria Justribó, Silvina C. Pellegrinet, and María I. Colombo
pp 3702–3712
Publication Date (Web): April 17, 2007 (Article)
DOI: 10.1021/jo062669f

Zinc(II) Perchlorate Hexahydrate Catalyzed Opening of Epoxide Ring by Amines:  Applications to Synthesis of (RS)/(R)-Propranolols and (RS)/(R)/(S)-Naftopidils

Shivani, Brahmam Pujala, and Asit K. Chakraborti
pp 3713–3722
Publication Date (Web): April 06, 2007 (Article)
DOI: 10.1021/jo062674j

Solid-Phase Synthesis of N-Nosyl- and N-Fmoc-N-Methyl-α-amino Acids

Maria Luisa Di Gioia, Antonella Leggio, Angelo Liguori, and Francesca Perri
pp 3723–3728
Publication Date (Web): April 17, 2007 (Article)
DOI: 10.1021/jo070075m

Highly Enantioselective Pd-Catalyzed Asymmetric Hydrogenation of Activated Imines

You-Qing Wang, Sheng-Mei Lu, and Yong-Gui Zhou
pp 3729–3734
Publication Date (Web): April 20, 2007 (Article)
DOI: 10.1021/jo0700878

Perfluoroalkylated 4,13-Diaza-18-Crown-6 Ethers:  Synthesis, Phase-Transfer Catalysis, and Recycling Studies

Alison M. Stuart and José A. Vidal
pp 3735–3740
Publication Date (Web): April 17, 2007 (Article)
DOI: 10.1021/jo062606x

Preparation and Diels−Alder Chemistry of 4-Vinylimidazoles

Carl J. Lovely, Hongwang Du, Rasapalli Sivappa, Manojkumar R. Bhandari, Yong He, and H. V. Rasika Dias
pp 3741–3749
Publication Date (Web): April 11, 2007 (Article)
DOI: 10.1021/jo0626008

Reducing Power of Simple Polyphenols by Electron-Transfer Reactions Using a New Stable Radical of the PTM Series, Tris(2,3,5,6-tetrachloro-4-nitrophenyl)methyl Radical

Josep Lluís Torres, Anna Carreras, Aurora Jiménez, Enric Brillas, Xavier Torrelles, Jordi Rius, and Luis Juliá
pp 3750–3756
Publication Date (Web): April 17, 2007 (Article)
DOI: 10.1021/jo062665a

Efficient Functionalizations of Heteroatom-Bridged Calix[2]arene[2]triazines on the Larger Rim

Hai-Bo Yang, De-Xian Wang, Qi-Qiang Wang, and Mei-Xiang Wang
pp 3757–3763
Publication Date (Web): April 11, 2007 (Article)
DOI: 10.1021/jo070001a

Studies on the Thermal Ring-Opening Reactions of cis-3,4-Bis(organosilyl)cyclobutenes

Munehiro Hasegawa and Masahiro Murakami
pp 3764–3769
Publication Date (Web): April 14, 2007 (Article)
DOI: 10.1021/jo070039n

First Total Synthesis and Assignment of the Stereochemistry of Crispatenine

Julien Bourdron, Laurent Commeiras, Gérard Audran, Nicolas Vanthuyne, J. C. Hubaud, and Jean-Luc Parrain
pp 3770–3775
Publication Date (Web): April 19, 2007 (Article)
DOI: 10.1021/jo070045j

Identification, Synthesis, and Conformation of Tri- and Tetrathiacycloalkanes from Marine Bacteria

Paul Sobik, Jörg Grunenberg, Katalin Böröczky, Hartmut Laatsch, Irene Wagner-Döbler, and Stefan Schulz
pp 3776–3782
Publication Date (Web): April 12, 2007 (Article)
DOI: 10.1021/jo070048w

Divergent Strategy for the Synthesis of α-Aryl-Substituted Fosmidomycin Analogues

Vincent Devreux, Jochen Wiesner, Hassan Jomaa, Jef Rozenski, Johan Van der Eycken, and Serge Van Calenbergh
pp 3783–3789
Publication Date (Web): April 12, 2007 (Article)
DOI: 10.1021/jo0700981

Double Dearomatization of Bis(diphenylphosphinamides) through Anionic Cyclization. A Facile Route of Accessing Multifunctional Systems with Antitumor Properties

Gloria Ruiz-Gómez, María José Iglesias, Manuel Serrano-Ruiz, Santiago García-Granda, Andrés Francesch, Fernando López-Ortiz, and Carmen Cuevas
pp 3790–3799
Publication Date (Web): April 18, 2007 (Article)
DOI: 10.1021/jo070276q

Intramolecular General Acid Catalysis of the Hydrolysis of 2-(2‘-Imidazolium)phenyl Phosphate, and Bond Length−Reactivity Correlations for Reactions of Phosphate Monoester Monoanions

Tiago A. S. Brandão, Elisa S. Orth, Willian R. Rocha, Adailton J. Bortoluzzi, Clifford A. Bunton, and Faruk Nome
pp 3800–3807
Publication Date (Web): April 14, 2007 (Article)
DOI: 10.1021/jo070090r

Explorations on the Asymmetric Total Synthesis of Isoschizogamine

Jianguang Zhou and Nabi A. Magomedov
pp 3808–3815
Publication Date (Web): April 12, 2007 (Article)
DOI: 10.1021/jo070144x

Titanocene(II)-Promoted Stereoselective Alkenylation Utilizing (Z)-Alkenyl Sulfones

Akitoshi Ogata, Masami Nemoto, Kenji Kobayashi, Akira Tsubouchi, and Takeshi Takeda
pp 3816–3822
Publication Date (Web): April 13, 2007 (Article)
DOI: 10.1021/jo070149u

Aminolyses of Aryl Diphenylphosphinates and Diphenylphosphinothioates:  Effect of Modification of Electrophilic Center from PO to PS

Ik-Hwan Um, Kalsoom Akhtar, Young-Hee Shin, and Jeong-Yoon Han
pp 3823–3829
Publication Date (Web): April 11, 2007 (Article)
DOI: 10.1021/jo070171n

New Dimeric Compounds of Avenanthramide Phytoalexin in Oats

Yozo Okazaki, Akihiro Ishizuka, Atsushi Ishihara, Takaaki Nishioka, and Hajime Iwamura
pp 3830–3839
Publication Date (Web): April 14, 2007 (Article)
DOI: 10.1021/jo0701740

Highly Efficient Retro-cycloaddition Reaction of Isoxazolino[4,5:1,2][60]- and -[70]fullerenes

Nazario Martín, Margarita Altable, Salvatore Filippone, Angel Martín-Domenech, Roberto Martínez-Álvarez, Margarita Suarez, Marta E. Plonska-Brzezinska, Olena Lukoyanova, and Luis Echegoyen
pp 3840–3846
Publication Date (Web): March 27, 2007 (Article)
DOI: 10.1021/jo070161m

Control of Surface Functionality in Poly(phenylenevinylene) Dendritic Architectures

Juan Tolosa, Carlos Romero-Nieto, Enrique Díez-Barra, Prado Sánchez-Verdú, and Julián Rodríguez-López
pp 3847–3852
Publication Date (Web): April 18, 2007 (Article)
DOI: 10.1021/jo070210v

A Highly Stereoselective Synthesis of (−)-(ent)-Julifloridine from the Cyclization of an Alanine-Derived Chloroamine with an Acetylenic Sulfone

Huimin Zhai, Masood Parvez, and Thomas G. Back
pp 3853–3858
Publication Date (Web): April 17, 2007 (Article)
DOI: 10.1021/jo0703101

Asymmetric Route to Pyridines Bearing a Highly Functionalized 2-Alkyl Substituent by Aziridine Ring-Opening Reactions

Diego Savoia, Giuseppe Alvaro, Romano Di Fabio, and Andrea Gualandi
pp 3859–3862
Publication Date (Web): April 14, 2007 (Article)
DOI: 10.1021/jo070364a

A β-Keto Ester as a Novel, Efficient, and Versatile Ligand for Copper(I)-Catalyzed C−N, C−O, and C−S Coupling Reactions

Xin Lv and Weiliang Bao
pp 3863–3867
Publication Date (Web): April 14, 2007 (Article)
DOI: 10.1021/jo070443m

Regiocontrol of the Palladium-Catalyzed Tin Hydride Addition to Z-Enynols:  Remarkable Z-Directing Effects

Abdallah Hamze, Olivier Provot, Jean-Daniel Brion, and Mouâd Alami
pp 3868–3874
Publication Date (Web): April 14, 2007 (Article)
DOI: 10.1021/jo0701435

Enantio- and Regioselective Heck-Type Reaction of Arylboronic Acids with 2,3-Dihydrofuran

Liza Penn, Alina Shpruhman, and Dmitri Gelman
pp 3875–3879
Publication Date (Web): April 10, 2007 (Article)
DOI: 10.1021/jo070170v

Triptycene-Based Expanded Oxacalixarenes:  Synthesis, Structure, and Tubular Assemblies in the Solid State

Chun Zhang and Chuan-Feng Chen
pp 3880–3888
Publication Date (Web): April 14, 2007 (Article)
DOI: 10.1021/jo0702490

Selective Sensing of Citrate by a Supramolecular 1,8-Naphthalimide/Calix[4]arene Assembly via Complexation-Modulated pKa Shifts in a Ternary Complex

Apurba L. Koner, Jürgen Schatz, Werner M. Nau, and Uwe Pischel
pp 3889–3895
Publication Date (Web): April 14, 2007 (Article)
DOI: 10.1021/jo070268+

Pyrrolidine and Piperidine Formation via Copper(II) Carboxylate-Promoted Intramolecular Carboamination of Unactivated Olefins:  Diastereoselectivity and Mechanism

Eric S. Sherman, Peter H. Fuller, Dhanalakshmi Kasi, and Sherry R. Chemler
pp 3896–3905
Publication Date (Web): April 12, 2007 (Article)
DOI: 10.1021/jo070321u

Notes

Investigation of Sulfur Extrusion from a Cyclic Dialkoxy Disulfide

Nicolas Eghbali and David N. Harpp
pp 3906–3908
Publication Date (Web): April 06, 2007 (Note)
DOI: 10.1021/jo062190n

Synthesis of Biologically Active Peptide Nucleic Acid−Peptide Conjugates by Sortase-Mediated Ligation

Stephan Pritz, Yvonne Wolf, Oliver Kraetke, Jana Klose, Michael Bienert, and Michael Beyermann
pp 3909–3912
Publication Date (Web): April 14, 2007 (Note)
DOI: 10.1021/jo062331l

Expeditious Access to Unprotected Racemic Pyroglutamic Acids

Jerry Isaacson, Cynthia B. Gilley, and Yoshihisa Kobayashi
pp 3913–3916
Publication Date (Web): April 07, 2007 (Note)
DOI: 10.1021/jo0700225

Facile Synthesis of Janus “Double-Concave” Tribenzo[a,g,m]coronenes

Zhongtao Li, Nigel T. Lucas, Zhaohui Wang, and Daoben Zhu
pp 3917–3920
Publication Date (Web): April 17, 2007 (Note)
DOI: 10.1021/jo0701029

A New Unusual Natural Pigment from Selaginella sinensis and Its Noticeable Physicochemical Properties

Li-Ping Zhang, Yong-Min Liang, Xiu-Cheng Wei, and Dong-Liang Cheng
pp 3921–3924
Publication Date (Web): April 17, 2007 (Note)
DOI: 10.1021/jo0701177

Trichloromethyltrimethylsilane, Sodium Formate, and Dimethylformamide:  A Mild, Efficient, and General Method for the Preparation of Trimethylsilyl-Protected 2,2,2-Trichloromethylcarbinols from Aldehydes and Ketones

Jérémy Kister and Charles Mioskowski
pp 3925–3928
Publication Date (Web): April 20, 2007 (Note)
DOI: 10.1021/jo070180w

Reactions of Nitroso Hetero-Diels−Alder Cycloadducts with Azides:  Stereoselective Formation of Triazolines and Aziridines

Brian S. Bodnar and Marvin J. Miller
pp 3929–3932
Publication Date (Web): April 13, 2007 (Note)
DOI: 10.1021/jo0701987

A Tricatecholic Receptor for Carbohydrate Recognition:  Synthesis and Binding Studies

Martina Cacciarini, Elisa Cordiano, Cristina Nativi, and Stefano Roelens
pp 3933–3936
Publication Date (Web): April 20, 2007 (Note)
DOI: 10.1021/jo0702286

Optimizing Biomimetic Gelators Constructed from Amino Acid Building Blocks

Ian A. Coates, Andrew R. Hirst, and David K. Smith
pp 3937–3940
Publication Date (Web): April 18, 2007 (Note)
DOI: 10.1021/jo070317i

Microwave-Assisted Piloty−Robinson Synthesis of 3,4-Disubstituted Pyrroles

Benjamin C. Milgram, Katrine Eskildsen, Steven M. Richter, W. Robert Scheidt, and Karl A. Scheidt
pp 3941–3944
Publication Date (Web): April 14, 2007 (Note)
DOI: 10.1021/jo070389+

Direct and Facile Syntheses of Heterocyclic Vinyl-C-Nucleosides for Recognition of Inverted Base Pairs by DNA Triple Helix Formation:  First Report by Direct Wittig Route

Jeffrey H. Rothman
pp 3945–3948
Publication Date (Web): April 14, 2007 (Note)
DOI: 10.1021/jo062206+

Synthesis of Z-5-Carboxymethylene-1,3-dioxolan-4-ones:  A Better Way

Keming Zhu, James H. Simpson, Edward J. Delaney, and William A. Nugent
pp 3949–3951
Publication Date (Web): April 14, 2007 (Note)
DOI: 10.1021/jo0700171

Facile Synthesis of (±)-Paeonilide

Yuguo Du, Jun Liu, and Robert J. Linhardt
pp 3952–3954
Publication Date (Web): April 06, 2007 (Note)
DOI: 10.1021/jo0701278

A Facile Approach to the Synthesis of Chiral 2-Substituted Benzofurans

Lidia De Luca, Giampaolo Giacomelli, and Giammario Nieddu
pp 3955–3957
Publication Date (Web): April 10, 2007 (Note)
DOI: 10.1021/jo070142c

First Example of Direct RuO4-Catalyzed Oxidation of Isoxazolidines to 3-Isoxazolidones

Anna Piperno, Ugo Chiacchio, Daniela Iannazzo, Salvatore V. Giofrè, Giovanni Romeo, and Roberto Romeo
pp 3958–3960
Publication Date (Web): April 10, 2007 (Note)
DOI: 10.1021/jo070211n

Reaction of 2,3-Allenoates with TsNBr2 in the Presence of Base:  A Facile Highly Stereoselective Synthesis of (1E,2E)-3-Bromo-4-oxo-N‘-tosyl-2-alkenoxylimidic Acid Ethyl Esters

Ruwei Shen and Xian Huang
pp 3961–3964
Publication Date (Web): April 13, 2007 (Note)
DOI: 10.1021/jo070239z

A Novel Multicomponent Reaction of Arynes, β-Keto Sulfones, and Michael-Type Acceptors:  A Direct Synthesis of Polysubstituted Naphthols and Naphthalenes

Xian Huang and Jian Xue
pp 3965–3968
Publication Date (Web): April 12, 2007 (Note)
DOI: 10.1021/jo070241q

Isothiocyanates from Tosyl Chloride Mediated Decomposition of in Situ Generated Dithiocarbamic Acid Salts

Rince Wong and Sarah J. Dolman
pp 3969–3971
Publication Date (Web): April 20, 2007 (Note)
DOI: 10.1021/jo070246n

Total Synthesis of Marine Sponge Bis(indole) Alkaloids of the Topsentin Class

Xavier Guinchard, Yannick Vallée, and Jean-Noël Denis
pp 3972–3975
Publication Date (Web): April 20, 2007 (Note)
DOI: 10.1021/jo070286r

Copper-Mediated Synthesis of Tertiary Diaryl Squaramides

Vijayakumar Ramalingam, Niala Bhagirath, and Rajeev S. Muthyala
pp 3976–3979
Publication Date (Web): April 10, 2007 (Note)
DOI: 10.1021/jo070393l

Additions and Corrections

Synthetic 3-O-Methylmannose-Containing Polysaccharides (sMMPs):  Design and Synthesis.

Margaret C. Hsu, Jinhwa Lee, and Yoshito Kishi.
p 3980
Publication Date (Web): April 14, 2007 (Addition/Correction)
DOI: 10.1021/jo070710o
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