Table of Contents

May 3, 2002
Volume 67, Issue 9
Pages 2735-3168

About the Cover: An efficient convergent synthesis of callystatin A, a potent cytotoxic polyketide isolated from the sponge Callyspongia truncata, employs chiral allenylzinc and tin reagents for key stereochemically defining and carbon-carbon bond-forming steps. See Marshall and Bourbeau, p 2751.

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Articles

Unified Route to the Palmarumycin and Preussomerin Natural Products. Enantioselective Synthesis of (−)-Preussomerin G

Anthony G. M. Barrett, Frank Blaney, Andrew D. Campbell, Dieter Hamprecht, Thorsten Meyer, Andrew J. P. White, David Witty, and David J. Williams
pp 2735–2750
Publication Date (Web): April 03, 2002 (Article)
DOI: 10.1021/jo0110247

Total Synthesis of (−)-Callystatin A

James A. Marshall and Matthew P. Bourbeau
pp 2751–2754
Publication Date (Web): December 18, 2001 (Article)
DOI: 10.1021/jo016025d

Mechanisms of Acid Decomposition of Dithiocarbamates. 4. Theoretical Calculations on the Water-Catalyzed Reaction

José I. García and Eduardo Humeres
pp 2755–2761
Publication Date (Web): March 29, 2002 (Article)
DOI: 10.1021/jo016209s

Solvent-Dependent Dynamic Kinetic Asymmetric Transformation/Kinetic Resolution in Molybdenum-catalyzed Asymmetric Allylic Alkylations

David L. Hughes, Michael Palucki, Nobuyoshi Yasuda, Robert A. Reamer, and Paul J. Reider
pp 2762–2768
Publication Date (Web): March 15, 2002 (Article)
DOI: 10.1021/jo015871l

A New Atropisomeric P,N Ligand for Rhodium-Catalyzed Asymmetric Hydroboration

Fuk Yee Kwong, Qingchuan Yang, Thomas C. W. Mak, Albert S. C. Chan, and Kin Shing Chan
pp 2769–2777
Publication Date (Web): March 28, 2002 (Article)
DOI: 10.1021/jo0159542

Cyclization/Hydrosilylation of Functionalized 1,6-Diynes Catalyzed by Cationic Platinum Complexes Containing Bidentate Nitrogen Ligands

Xiang Wang, Harinath Chakrapani, James W. Madine, Michele A. Keyerleber, and Ross A. Widenhoefer
pp 2778–2788
Publication Date (Web): April 04, 2002 (Article)
DOI: 10.1021/jo015986p

Diastereoselective Synthesis and Estimation of the Conformational Flexibility of 6-Oxoperhydropyridazine-3-carboxylic Acid Derivatives

Carlos Alvarez-Ibarra, Aurelio G. Csákÿ, and Cristina Gómez de la Oliva
pp 2789–2797
Publication Date (Web): April 06, 2002 (Article)
DOI: 10.1021/jo0159800

Structural and Electronic Characteristics of Thienyl(aryl)iodonium Triflates

Darren Bykowski, Robert McDonald, Robert J. Hinkle, and Rik R. Tykwinski
pp 2798–2804
Publication Date (Web): March 29, 2002 (Article)
DOI: 10.1021/jo015910t

Study of Cross-Conjugated iso-Polytriacetylenes and Related Oligoenynes

Yuming Zhao, Robert McDonald, and Rik R. Tykwinski
pp 2805–2812
Publication Date (Web): March 27, 2002 (Article)
DOI: 10.1021/jo015995y

Stereochemical Control of Reductions. 9. Haptophilicity Studies with 1,1-Disubstituted 2-Methyleneacenaphthenes

Hugh W. Thompson and Shaker Y. Rashid
pp 2813–2825
Publication Date (Web): April 02, 2002 (Article)
DOI: 10.1021/jo010633b

A New Approach to the Reduction of Sulfoxides to Sulfides with 1,3-Dithiane in the Presence of Electrophilic Bromine as Catalyst

Nasser Iranpoor, Habib Firouzabadi, and Hamid Reza Shaterian
pp 2826–2830
Publication Date (Web): April 10, 2002 (Article)
DOI: 10.1021/jo016027y

Chiral Lewis Acid Catalyzed Resolution of Racemic Enol Ester Epoxides. Conversion of Both Enantiomers of an Enol Ester Epoxide to the Same Enantiomer of Acyloxy Ketone

Xiaoming Feng, Lianhe Shu, and Yian Shi
pp 2831–2836
Publication Date (Web): March 30, 2002 (Article)
DOI: 10.1021/jo0108515

Control of Regioselectivity in Pd(0)-Catalyzed Coupling−Cyclization Reaction of 2-(2‘,3‘-Allenyl)malonates with Organic Halides

Shengming Ma, Ning Jiao, Shimin Zhao, and Hairong Hou
pp 2837–2847
Publication Date (Web): April 10, 2002 (Article)
DOI: 10.1021/jo0108616

Exploring the Active Site of Amine:Pyruvate Aminotransferase on the Basis of the Substrate Structure−Reactivity Relationship:  How the Enzyme Controls Substrate Specificity and Stereoselectivity

Jong-Shik Shin and Byung-Gee Kim
pp 2848–2853
Publication Date (Web): March 20, 2002 (Article)
DOI: 10.1021/jo016115i

Mechanism of the Second Sulfenylation of Indole

Pierre Hamel
pp 2854–2858
Publication Date (Web): April 11, 2002 (Article)
DOI: 10.1021/jo0109220

Preparation, Properties, and Chemical Reactivity of α-Nitrosulfoximines, Chiral Analogues of α-Nitrosulfones

Peter A. Wade, Hung Le, and Nayan V. Amin
pp 2859–2863
Publication Date (Web): March 27, 2002 (Article)
DOI: 10.1021/jo010924k

Preparation of a 24-Nor-1,4-dien-3-one Triterpene Derivative from Betulin:  A New Route to 24-Nortriterpene Analogues1

Yonghong Deng and John K. Snyder
pp 2864–2873
Publication Date (Web): April 11, 2002 (Article)
DOI: 10.1021/jo010929h

Total Synthesis of Spicamycin

Tamotsu Suzuki, Sayaka T. Suzuki, Iwao Yamada, Yoshiaki Koashi, Kazue Yamada, and Noritaka Chida
pp 2874–2880
Publication Date (Web): April 09, 2002 (Article)
DOI: 10.1021/jo010925c

Unusual Regioselective Intramolecular Diels−Alder Reaction Forming Tricyclo[4.3.1.03,7]decane System

Kiyosei Takasu, Sayaka Mizutani, and Masataka Ihara
pp 2881–2884
Publication Date (Web): April 05, 2002 (Article)
DOI: 10.1021/jo016129o

Nitrile Anions:  Solvent-Dependent Cyclizations

Fraser F. Fleming and Brian C. Shook
pp 2885–2888
Publication Date (Web): March 29, 2002 (Article)
DOI: 10.1021/jo016156e

Lewis Acid Promoted Cyclization of Enyne Triesters and Diesters

Shoko Yamazaki, Kuriko Yamada, and Shinichi YamabeKagetoshi Yamamoto
pp 2889–2901
Publication Date (Web): March 28, 2002 (Article)
DOI: 10.1021/jo016159r

A Facile Synthesis of Enantiopure 2-Aziridinesulfinimines and Their Highly Diastereoselective Reactions with Phosphite Anions

Bin-Feng Li, Ming-Jie Zhang, Xue-Long Hou, and Li-Xin Dai
pp 2902–2906
Publication Date (Web): March 28, 2002 (Article)
DOI: 10.1021/jo016106+

Syntheses and Bioactivities of Substituted 9,10-Dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrones. Unusual Reactivities with Amines

Duy H. Hua, Masafumi Tamura, Xiaodong Huang, Heidi A. Stephany, Brian A. Helfrich, Elisabeth M. Perchellet, Bonnie J. Sperfslage, Jean-Pierre Perchellet, Suping Jiang, Dennis E. Kyle, and Peter K. Chiang
pp 2907–2912
Publication Date (Web): April 06, 2002 (Article)
DOI: 10.1021/jo010958s

DFT Study of Substituted and Benzannelated Aryl Cations:  Substituent Dependency of Singlet/Triplet Ratio1a

Kenneth K. Laali, Golam Rasul, G. K. Surya Prakash, and George A. Olah
pp 2913–2918
Publication Date (Web): April 10, 2002 (Article)
DOI: 10.1021/jo020084p

Cyclic Vinyl p-Tolyl Sulfilimines as Chiral Dienophiles:  Diels−Alder Reactions with Furan and Acyclic Dienes

José L. García Ruano, Carlos Alemparte, Fernando R. Clemente, Lorena González Gutiérrez, Ruth Gordillo, Ana M. Martín Castro, and Jesús H. Rodríguez Ramos
pp 2919–2925
Publication Date (Web): March 28, 2002 (Article)
DOI: 10.1021/jo016174w

Cyclic Vinyl p-Tolyl Sulfilimines as Chiral Dienophiles:  Theoretical Study on the Stereoselectivity, Lewis Acid Catalysis, and Solvent Effects in Their Diels−Alder Reactions

José L. García Ruano, Fernando R. Clemente, Lorena González Gutiérrez, Ruth Gordillo, Ana M. Martín Castro, and Jesús H. Rodríguez Ramos
pp 2926–2933
Publication Date (Web): March 28, 2002 (Article)
DOI: 10.1021/jo016175o

Studies on the Formation and Incorporation of Streptolidine in the Biosynthesis of the Peptidyl Nucleoside Antibiotic Streptothricin F

Michael D. Jackson, Steven J. Gould, and T. Mark Zabriskie
pp 2934–2941
Publication Date (Web): March 19, 2002 (Article)
DOI: 10.1021/jo016182c

Electronic Effects in the N-Nitrosation of N-Benzylpivalamides

Ron W. Darbeau, Rebecca S. Pease, and Edson V. Perez
pp 2942–2947
Publication Date (Web): April 03, 2002 (Article)
DOI: 10.1021/jo011002k

Host−Guest Interactions between β-Cyclodextrin and the (Z)-Phenylhydrazone of 3-Benzoyl-5-phenyl-1,2,4-oxadiazole:  The First Kinetic Study of a Ring−Ring Interconversion in a “Confined Environment”

Susanna Guernelli, Maria Francesca Laganà, and Domenico SpinelliPaolo Lo Meo, Renato Noto, and Serena Riela
pp 2948–2953
Publication Date (Web): March 29, 2002 (Article)
DOI: 10.1021/jo016214w

Total Synthesis of (S)-(+)-Imperanene. Effective Use of Regio- and Enantioselective Intramolecular Carbon−Hydrogen Insertion Reactions Catalyzed by Chiral Dirhodium(II) Carboxamidates

Michael P. Doyle, Wenhao Hu, and Marcela V. Valenzuela
pp 2954–2959
Publication Date (Web): April 02, 2002 (Article)
DOI: 10.1021/jo016220s

A Solid-Phase Synthetic Route to Unnatural Amino Acids with Diverse Side-Chain Substitutions

William L. ScottMartin J. O'Donnell, Francisca Delgado, and Jordi Alsina
pp 2960–2969
Publication Date (Web): April 03, 2002 (Article)
DOI: 10.1021/jo016236i

Role of NaBH4 Stabilizer in the Oxazaborolidine-Catalyzed Asymmetric Reduction of Ketones with BH3-THF

Shawn M. Nettles, Karl Matos, Elizabeth R. Burkhardt, Dave R. Rouda, and Joseph A. Corella
pp 2970–2976
Publication Date (Web): April 05, 2002 (Article)
DOI: 10.1021/jo016257c

Tricycloclavulone and Clavubicyclone, Novel Prostanoid-Related Marine Oxylipins, Isolated from the Okinawan Soft Coral Clavularia viridis

Makoto Iwashima, Ikuo Terada, Katsumi Okamoto, and Kazuo Iguchi
pp 2977–2981
Publication Date (Web): April 03, 2002 (Article)
DOI: 10.1021/jo011043g

Stereocontrol at the Steady State in Radical Cyclizations of Acyclic Dihalides

Krzysztof Stalinski and Dennis P. Curran
pp 2982–2988
Publication Date (Web): March 28, 2002 (Article)
DOI: 10.1021/jo011056u

Allylation of Exocyclic N-Acyliminium Ions Generated from Chiral N-[1-(Phenylsulfonyl)alkyl]oxazolidin-2-ones

Enrico Marcantoni, Tiziana Mecozzi, and Marino Petrini
pp 2989–2994
Publication Date (Web): April 11, 2002 (Article)
DOI: 10.1021/jo0162888

Synthesis of α-GalNAc Thioconjugates from an α-GalNAc Mercaptan

Spencer Knapp and David S. Myers
pp 2995–2999
Publication Date (Web): April 11, 2002 (Article)
DOI: 10.1021/jo0110909

Diastereoselective Reactions of δ-Oxy-Substituted Allylic Acetates with Organocopper Reagents

Jennifer L. Belelie and J. Michael Chong
pp 3000–3006
Publication Date (Web): April 05, 2002 (Article)
DOI: 10.1021/jo016310x

Cross-Linking of Proteins by 3-(Trifluoromethyl)-2,5-hexanedione. Model Studies Implicate an Unexpected Amine-Dependent Defluorinative Substitution Pathway Competing with Pyrrole Formation

Guozhang Xu and Lawrence M. Sayre
pp 3007–3014
Publication Date (Web): March 23, 2002 (Article)
DOI: 10.1021/jo011101y

Synthesis of Optically Active Vicinal Fluorohydrins by Lipase-Catalyzed Deracemization

Dörthe Wölker and Günter Haufe
pp 3015–3021
Publication Date (Web): April 06, 2002 (Article)
DOI: 10.1021/jo016331r

Selectivity of Biohydroxylation with Beauveria bassiana of trans-2-Fluorocycloalkyl N-Phenylcarbamates

Günter Haufe, Dörthe Wölker, and Roland Fröhlich
pp 3022–3028
Publication Date (Web): April 06, 2002 (Article)
DOI: 10.1021/jo016332j

Nickel(0)/Dihydroimidazol-2-ylidene Complex Catalyzed Coupling of Aryl Chlorides and Amines

Christophe Desmarets, Raphaël Schneider, and Yves Fort
pp 3029–3036
Publication Date (Web): March 29, 2002 (Article)
DOI: 10.1021/jo016352l

Synthesis of Diazadibenzoperylenes and Characterization of Their Structural, Optical, Redox, and Coordination Properties

Frank Würthner, Armin Sautter, and Joachim Schilling
pp 3037–3044
Publication Date (Web): April 10, 2002 (Article)
DOI: 10.1021/jo011133l

Preparation of New Microgel Polymers and Their Application as Supports in Organic Synthesis

Carsten Spanka, Bruce Clapham, and Kim D. Janda
pp 3045–3050
Publication Date (Web): March 30, 2002 (Article)
DOI: 10.1021/jo016362m

Carbenoid Reactions of 2-Halomethyl-4,6-dimethyl-s-triazines

Craig L. Stephens, H. LeRoy Nyquist, and Kenneth I. Hardcastle
pp 3051–3056
Publication Date (Web): April 02, 2002 (Article)
DOI: 10.1021/jo0111412

Peptidotriazoles on Solid Phase:  [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides

Christian W. Tornøe, Caspar Christensen, and Morten Meldal
pp 3057–3064
Publication Date (Web): April 02, 2002 (Article)
DOI: 10.1021/jo011148j

Studies toward the Synthesis of α-Fluorinated Phosphonates via Tin-Mediated Cleavage of α-Fluoro-α-(pyrimidin-2-ylsulfonyl)alkylphosphonates. Intramolecular Cyclization of the α-Phosphonyl Radicals

Stanislaw F. Wnuk, Luis A. Bergolla, and Pedro I. Garcia, Jr.
pp 3065–3071
Publication Date (Web): March 27, 2002 (Article)
DOI: 10.1021/jo0111560

Conformational Control of Flexible Molecules:  Design and Synthesis of Novel Chiral 1,5-Diaza-cis-decalins

Zhenrong Xu and Marisa C. Kozlowski
pp 3072–3078
Publication Date (Web): March 16, 2002 (Article)
DOI: 10.1021/jo025503x

Computational and Experimental Studies of the Effect of Substituents on the Singlet−Triplet Energy Gap in Phenyl(carbomethoxy)carbene

C. Michael Geise, Yuhong Wang, Olena Mykhaylova, Brian T. Frink, John P. Toscano, and Christopher M. Hadad
pp 3079–3088
Publication Date (Web): April 05, 2002 (Article)
DOI: 10.1021/jo0255330

Conformational Studies by Dynamic NMR. 89.1 Stereomutation and Cryogenic Enantioseparation of Conformational Antipodes of Hindered Aryl Oximes

Francesco Gasparrini, Stefano Grilli, Rino Leardini, Lodovico Lunazzi, Andrea Mazzanti, Daniele Nanni, Marco Pierini, and Marco Pinamonti
pp 3089–3095
Publication Date (Web): March 30, 2002 (Article)
DOI: 10.1021/jo0255431

Wittig-Type Olefination Catalyzed by PEG-telluride

Zheng-Zheng Huang, Song Ye, Wei Xia, Yi-Hua Yu, and Yong Tang
pp 3096–3103
Publication Date (Web): March 30, 2002 (Article)
DOI: 10.1021/jo025586h

1,2- vs 1,4-Addition of Acylbenzotriazoles to α,β-Unsaturated Aldehydes and Ketones. A Novel Route to 3-Alkyl-4,6-diaryl-3,4-dihydropyran-2-ones

Alan R. Katritzky and Olga V. Denisko
pp 3104–3108
Publication Date (Web): April 06, 2002 (Article)
DOI: 10.1021/jo011082s

Convenient Syntheses of Unsymmetrical Imidazolidines

Alan R. Katritzky, Kazuyuki Suzuki, and Hai-Ying He
pp 3109–3114
Publication Date (Web): April 06, 2002 (Article)
DOI: 10.1021/jo010868n

Notes

Novel Syntheses of Hexahydropyrimidines and Tetrahydroquinazolines

Alan R. Katritzky, Sandeep K. Singh, and Hai-Ying He
pp 3115–3117
Publication Date (Web): April 06, 2002 (Note)
DOI: 10.1021/jo010927x

A Novel Rearrangement to 1,2,4-Triazolo[1,5-a]quinoxalines

Alan R. Katritzky, Tian-Bao Huang, and Olga V. DeniskoPeter J. Steel
pp 3118–3119
Publication Date (Web): April 06, 2002 (Note)
DOI: 10.1021/jo011028b

Designed, Folded Polypeptide Scaffolds That Combine Key Biosensing Events of Recognition and Reporting

Karin Enander, Gunnar T. Dolphin, Linda K. Andersson, Bo Liedberg, Ingemar Lundström, and Lars Baltzer
pp 3120–3123
Publication Date (Web): April 02, 2002 (Note)
DOI: 10.1021/jo010954n

Acid-Catalyzed Formation of Hexahomooxacalix[3]arenes

Mijan Miah, Nikolai N. Romanov, and Peter J. Cragg
pp 3124–3126
Publication Date (Web): March 28, 2002 (Note)
DOI: 10.1021/jo025597a

Synthesis of 4-Acetylisocoumarin:  First Total Syntheses of AGI-7 and Sescandelin

Sanghee Kim, Gao-jun Fan, Jaekwang Lee, Jung Joon Lee, and Deukjoon Kim
pp 3127–3130
Publication Date (Web): March 29, 2002 (Note)
DOI: 10.1021/jo010789b

Practical Asymmetric Synthesis of the Herbicide (S)-Indanofan via Lipase-Catalyzed Kinetic Resolution of a Diol and Stereoselective Acid-Catalyzed Hydrolysis of a Chiral Epoxide

Ken Tanaka, Kenji Yoshida, Chiduko Sasaki, and Yasuko T. Osano
pp 3131–3133
Publication Date (Web): April 10, 2002 (Note)
DOI: 10.1021/jo010816y

A Preliminary Approach to Nonenolizable β,β-Tricarbonyls:  Assembly of a Hyperevolutin Prototype1

David G. J. Young and Dongxiang Zeng
pp 3134–3137
Publication Date (Web): April 05, 2002 (Note)
DOI: 10.1021/jo010884k

Solid-Phase Synthesis of 1,5-Disubstituted 2-Aryliminoimidazolidines

Yongping Yu, John M. Ostresh, and Richard A. Houghten
pp 3138–3141
Publication Date (Web): April 02, 2002 (Note)
DOI: 10.1021/jo0109366

An Improved Synthesis of Cyclopropanes from Stabilized Phosphonates and 1,2-Dioxines

Marc C. Kimber and Dennis K. Taylor
pp 3142–3144
Publication Date (Web): April 09, 2002 (Note)
DOI: 10.1021/jo0110496

A Study of the Ionic Liquid Mediated Microwave Heating of Organic Solvents

Nicholas E. Leadbeater and Hanna M. Torenius
pp 3145–3148
Publication Date (Web): April 09, 2002 (Note)
DOI: 10.1021/jo016297g

Trimethylsilylethynyl Ketones as Surrogates for Ethynyl Ketones in the Double Michael Reaction

Derrick S. Holeman, Ravindra M. Rasne, and Robert B. Grossman
pp 3149–3151
Publication Date (Web): April 05, 2002 (Note)
DOI: 10.1021/jo0163086

Application of Ruthenium-Induced Macrocyclization for the Construction of Macrocyclic Depsipeptides

Srikanth Venkatraman, F. George Njoroge, Viyyoor Girijavallabhan, and Andrew T. McPhail
pp 3152–3155
Publication Date (Web): March 27, 2002 (Note)
DOI: 10.1021/jo011106v

Convenient Synthesis of 3,3,3-Trifluoropropenyl Compounds from Aromatic Aldehydes by Means of the TBAF-Mediated Horner Reaction

Tetsuya Kobayashi, Takuya Eda, Osamu Tamura, and Hiroyuki Ishibashi
pp 3156–3159
Publication Date (Web): April 11, 2002 (Note)
DOI: 10.1021/jo0111311

Facile Synthesis of Novel Functionalized Bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF) Derivatives

Shi-Xia Liu, Stefan Dolder, Melanie Pilkington, and Silvio Decurtins
pp 3160–3162
Publication Date (Web): April 04, 2002 (Note)
DOI: 10.1021/jo0163694

Wilkinson's Catalyst Catalyzed Selective Hydrogenation of Olefin in the Presence of an Aromatic Nitro Function:  A Remarkable Solvent Effect

Angélique Jourdant, Eduardo González-Zamora, and Jieping Zhu
pp 3163–3164
Publication Date (Web): April 11, 2002 (Note)
DOI: 10.1021/jo025595q

Syntheses and Conformations of Tetrahomodioxacalix[4]arene Tetraamides and Tetrathioamides

Kwanghyun No, Jeong Hyeon Lee, Seung Hwan Yang, Sang Hyeok Yu, Moon Hwan Cho, Moon Jib Kim, and Jong Seung Kim
pp 3165–3168
Publication Date (Web): April 11, 2002 (Note)
DOI: 10.1021/jo011138i
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