Table of Contents

June 12, 1998
Volume 63, Issue 12
Pages 3796-4162
For Selected Content:

Articles

A Convenient Asymmetric Synthesis of 4‘-α-Carboxylated Nucleosides

David Crich and Xiaolin Hao
pp 3796–3797
Publication Date (Web): May 20, 1998 (Communication)
DOI: 10.1021/jo980301f

Stereospecific Synthesis of 2,3-Dihydro-4H-pyran-4-ones by Hg(II)- Catalyzed Rearrangement of 1-Alkynyl-2,3-epoxy Alcohols

Charles M. Marson, Steven Harper, and Catriona A. OareTimothy Walsgrove
pp 3798–3799
Publication Date (Web): May 20, 1998 (Communication)
DOI: 10.1021/jo9715837

Concerning the Synthesis of the Elusive anti,anti-Dipropionate Stereotriad via the Crotylation of β-Hydroxy α-Methyl Aldehydes with (Z)-Crotyltrifluorosilane. Application to the Synthesis of the C(7)−C(16) Segment of Zincophorin

Sherry R. Chemler and William R. Roush
pp 3800–3801
Publication Date (Web): May 27, 1998 (Communication)
DOI: 10.1021/jo980387c

Cooperative Control of Ion and Molecular Recognition by Molecular Assembling

Tatsuya Nabeshima, Takayoshi Takahashi, Takeshi Hanami, Akihiro Kikuchi, Tohru Kawabe, and Yumihiko Yano
pp 3802–3803
Publication Date (Web): May 20, 1998 (Communication)
DOI: 10.1021/jo980406i

Diprotected Triflylguanidines:  A New Class of Guanidinylation Reagents

Konrad Feichtinger, Christoph Zapf, Heather L. Sings, and Murray Goodman
pp 3804–3805
Publication Date (Web): May 27, 1998 (Communication)
DOI: 10.1021/jo980425s

Efficient Preparation of Functionalized (E,Z) Dienes Using Acetylene as the Building Block

Zhong Wang, Xiyan Lu, Aiwen Lei, and Zhaoguo Zhang
pp 3806–3807
Publication Date (Web): May 28, 1998 (Communication)
DOI: 10.1021/jo980440x

Metalated Epoxides as Carbenoids. Solvent Effect on the Alkyl 1,2-Shift in α-Hydroxy Epoxide Systems

Eric Doris and Charles MioskowskiLuc Dechoux and Claude Agami
pp 3808–3809
Publication Date (Web): May 27, 1998 (Communication)
DOI: 10.1021/jo9805596

Diels−Alder Reactions of 2-(N-Acylamino)-1,3-dienes. Atypical Regioselectivity and Endo/Exo Selectivity

Jae Du Ha, Chul Hyun Kang, Kenneth A. Belmore, and Jin Kun Cha
pp 3810–3811
Publication Date (Web): May 28, 1998 (Communication)
DOI: 10.1021/jo980593k

Synthesis of Chiral Enantioenriched Homopropargylic Alcohols from Propargylic Mesylates via Chiral Allenylzinc Intermediates

James A. Marshall and Nicholas D. Adams
pp 3812–3813
Publication Date (Web): May 15, 1998 (Communication)
DOI: 10.1021/jo980623j

Thermal Decomposition of tert-Butyl 1-Arylcycloalkanepercarboxylates

Richard A. Wolf, Richard J. Trocino, William R. Rozich, Isidore C. Sabeta, and Richard J. Ordway, Jr.
pp 3814–3820
Publication Date (Web): May 20, 1998 (Article)
DOI: 10.1021/jo970211v

Estimating the Entropic Cost of Self-Assembly of Multiparticle Hydrogen-Bonded Aggregates Based on the Cyanuric Acid·Melamine Lattice

Mathai Mammen, Eugene I. Shakhnovich, John M. Deutch, and George M. Whitesides
pp 3821–3830
Publication Date (Web): May 28, 1998 (Article)
DOI: 10.1021/jo970944f

An Investigation of the Diastereoselectivity of Nucleophilic Additions to 6-Methyl-1-oxa-4-thiaspiro[4.5]dec-6-ene-7-carbaldehyde. Hybridization of the Nucleophile Alters the Diastereoselectivity

Duraiswamy A. Jeyaraj, Veejendra K. Yadav, Masood Parvez, and Harsh M. Gauniyal
pp 3831–3837
Publication Date (Web): May 22, 1998 (Article)
DOI: 10.1021/jo971697i

D/H Exchange in Nitro Diastereomers

Charles A. Kingsbury
pp 3838–3846
Publication Date (Web): May 19, 1998 (Article)
DOI: 10.1021/jo9717402

Stereoselectivity of Triplet Photocycloadditions:1 Diene−Carbonyl Reactions and Solvent Effects

Axel G. Griesbeck, Stefan Buhr, Maren Fiege, Hans Schmickler, and Johann Lex
pp 3847–3854
Publication Date (Web): May 20, 1998 (Article)
DOI: 10.1021/jo971767l

Convenient Synthesis of an A-Ring Aromatic Trichothecene Analog

Jayati Mal and Ramanathapuram V. Venkateswaran
pp 3855–3858
Publication Date (Web): May 19, 1998 (Article)
DOI: 10.1021/jo971970g

Thermochemistry of Sulfenic Esters (RSOR‘):  Not Just Another Pretty Peroxide

Daniel D. Gregory and William S. Jenks
pp 3859–3865
Publication Date (Web): May 27, 1998 (Article)
DOI: 10.1021/jo9720243

Conformation and Stereodynamics of Monodioxamethylene Calix[4]arene Derivatives

Jens Wöhnert, Jörg Brenn, Matthias Stoldt, Oleg Aleksiuk, Flavio Grynszpan, Iris Thondorf, and Silvio E. Biali
pp 3866–3874
Publication Date (Web): May 19, 1998 (Article)
DOI: 10.1021/jo9720602

Molecular Orbital Studies of the Intramolecular Reaction of Protonated cis- and trans-3,4-Epoxypentan-1-ol

James M. Coxon, Keiji Morokuma, Aaron J. Thorpe, and Dale Whalen
pp 3875–3883
Publication Date (Web): May 22, 1998 (Article)
DOI: 10.1021/jo972071v

Ag+-Specific Pyridine Podands:  Effects of Ligand Geometry and Stereochemically Controlled Substitution on Cation Complexation and Transport Functions

Hiroshi Tsukube, Satoshi Shinoda, Jun'ichi Uenishi, Takao Hiraoka, Takahiro Imakoga, and Osamu Yonemitsu
pp 3884–3894
Publication Date (Web): May 22, 1998 (Article)
DOI: 10.1021/jo9721148

A New Family of Enantiomerically Pure Smectic C* Liquid Crystals with a Bridged Chiral Biphenyl Core

Guy Solladié, Philippe Hugelé, and Richard Bartsch
pp 3895–3898
Publication Date (Web): May 15, 1998 (Article)
DOI: 10.1021/jo972143i

Diastereomer-Differentiating Radical β-Addition to 4- or 5-Methyl-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2-cyclopentenones

Nobuyuki Mase, Yoshihiko Watanabe, and Takeshi Toru
pp 3899–3904
Publication Date (Web): May 21, 1998 (Article)
DOI: 10.1021/jo9721507

Photochemical Electron-Transfer Reactions between Sulfides and Tetranitromethane. Oxidation vs Fragmentation of the Sulfide Radical-Cation Intermediate

Waldemar Adam, Juan E. Argüello, and Alicia B. Peñéñory
pp 3905–3910
Publication Date (Web): May 19, 1998 (Article)
DOI: 10.1021/jo972183m

Iodothyronine Deiodinase Mimics. Deiodination of o,o‘-Diiodophenols by Selenium and Tellurium Reagents

Andrei A. Vasil'ev and Lars Engman
pp 3911–3917
Publication Date (Web): May 15, 1998 (Article)
DOI: 10.1021/jo972240b

Enantioselective Synthesis of Substituted Pipecolic Acid Derivatives

José Barluenga, Fernando Aznar, Carlos Valdés, and Cristina Ribas
pp 3918–3924
Publication Date (Web): May 23, 1998 (Article)
DOI: 10.1021/jo9722414

Absolute Structure and Total Synthesis of Lipogrammistin-A, a Lipophilic Ichthyotoxin of the Soapfish

Hiroyuki Onuki, Kei Ito, Yoshimasa Kobayashi, Nobuaki Matsumori, and Kazuo TachibanaNobuhiro Fusetani
pp 3925–3932
Publication Date (Web): May 15, 1998 (Article)
DOI: 10.1021/jo9722461

Conformational Studies by Dynamic NMR. 63.1 Stereodynamics of Dialkylamino Ethoxy Disulfides:  S−S and S−N Rotation Processes

G. CerioniM. A. CremoniniL. Lunazzi and G. PlacucciA. Plumitallo
pp 3933–3936
Publication Date (Web): May 27, 1998 (Article)
DOI: 10.1021/jo972259e

Effect of Fluorine Substitution on the Carbon Acidity of Methane, Methyl Isocyanide, Acetonitrile, Acetaldehyde, and Nitromethane

Henry J. Castejon and Kenneth B. Wiberg
pp 3937–3942
Publication Date (Web): May 20, 1998 (Article)
DOI: 10.1021/jo9722818

Interaction of Trimethylsilyl and Trimethylstannyl Substituents with C−O Bonds at the γ Position. Results from X-ray Structural Studies and Solvolysis Studies

Alison J. Green, Tracey Pigdon, Jonathan M. White, and Joseph Yamen
pp 3943–3951
Publication Date (Web): May 22, 1998 (Article)
DOI: 10.1021/jo9723265

New Tetrathiafulvalene Donors with Extended Peripheral Substituents by Addition of Heterocycles:  Synthesis, Properties, and Molecular Structures

Jun-ichi Yamada, Satoru Tanaka, Junko Segawa, Miho Hamasaki, Kenji Hagiya, Hiroyuki Anzai, Hiroyuki Nishikawa, Isao Ikemoto, and Koichi Kikuchi
pp 3952–3960
Publication Date (Web): May 27, 1998 (Article)
DOI: 10.1021/jo972337y

Direct Synthesis of α,β-Unsaturated Nitriles Catalyzed by Nonionic Superbases

Bosco A. D'Sa, Philip Kisanga, and John G. Verkade
pp 3961–3967
Publication Date (Web): May 19, 1998 (Article)
DOI: 10.1021/jo972343u

Generation and Mesolysis of PhSeSiR3]•-:  Mechanistic Studies by Laser Flash Photolysis and Application for Bimolecular Group Transfer Radical Reactions

Ganesh Pandey, K. S. Sesha Poleswara Rao, D. K. Palit, and J. P. Mittal
pp 3968–3978
Publication Date (Web): May 15, 1998 (Article)
DOI: 10.1021/jo972345e

A Synthesis of d-erythro- and l-threo-Sphingosine and Sphinganine Diastereomers via the Biomimetic Precursor 3-Ketosphinganine

Robert V. Hoffman and Junhua Tao
pp 3979–3985
Publication Date (Web): May 21, 1998 (Article)
DOI: 10.1021/jo980003i

IMDAF Cycloaddition as a Method for the Preparation of Pyrrolophenanthridine Alkaloids

Albert Padwa, Martin Dimitroff, Alex G. Waterson, and Tianhua Wu
pp 3986–3997
Publication Date (Web): May 21, 1998 (Article)
DOI: 10.1021/jo980008f

Porphyrins with Exocyclic Rings. 11.1 Synthesis and Characterization of Phenanthroporphyrins, a New Class of Modified Porphyrin Chromophores

Bennett H. Novak and Timothy D. Lash
pp 3998–4010
Publication Date (Web): May 20, 1998 (Article)
DOI: 10.1021/jo980043m

Aromatics to Triquinanes:  p-Cresol to (±)-Δ9(12)-Capnellene

Vishwakarma Singh, S. Prathap, and M. Porinchu
pp 4011–4017
Publication Date (Web): May 20, 1998 (Article)
DOI: 10.1021/jo980064g

Antitumor Agents. 183. Syntheses, Conformational Analyses, and Antitubulin Activity of Allothiocolchicinoids

Qian Shi, Ke Chen, Xin Chen, Arnold Brossi, Pascal Verdier-Pinard, Ernest Hamel, Andrew T. McPhail, Alexander Tropsha, and Kuo-Hsiung Lee
pp 4018–4025
Publication Date (Web): May 21, 1998 (Article)
DOI: 10.1021/jo980073p

Electron-Transfer-Photosensitized Conjugate Alkylation

Maurizio Fagnoni, Mariella Mella, and Angelo Albini
pp 4026–4033
Publication Date (Web): May 27, 1998 (Article)
DOI: 10.1021/jo980093r

A Modified Procedure for Sonogashira Couplings:  Synthesis and Characterization of a Bisporphyrin, 1,1-Bis[zinc(II) 5‘-ethynyl-10‘,15‘,20‘-trimesitylporphyrinyl]methylenecyclohexane

David A. Shultz, Kevin P. Gwaltney, and Hyoyoung Lee
pp 4034–4038
Publication Date (Web): May 15, 1998 (Article)
DOI: 10.1021/jo980098o

Kinetic Chiral Resolutions of 1,2-Diols and Desymmetrization of Glycerol Catalyzed by Glycerol Kinase

H. Keith Chenault, Laura F. Chafin, and Sebastian Liehr
pp 4039–4045
Publication Date (Web): May 19, 1998 (Article)
DOI: 10.1021/jo980122y

A Novel Strategy for the Synthesis of Molecules with Helical Chirality. Intramolecular [2 + 2 + 2] Cycloisomerization of Triynes under Cobalt Catalysis

Irena G. Stará, Ivo Starý, Adrian Kollárovi, Filip Teplý, David Šaman, and Miloš Tichý
pp 4046–4050
Publication Date (Web): May 22, 1998 (Article)
DOI: 10.1021/jo9801263

Thermally Induced Cyclodehydrogenation of Biaryls:  A Simple Radical Reaction or a Sequence of Rearrangements?

Jerzy Cioslowski, Pawel Piskorz, and David Moncrieff
pp 4051–4054
Publication Date (Web): May 28, 1998 (Article)
DOI: 10.1021/jo980132z

Preparation and Study of Tautomers Derived from 2-(2‘-Pyridyl)indole and Related Compounds

Feiyue Wu, Jon Hardesty, and Randolph P. Thummel
pp 4055–4061
Publication Date (Web): May 22, 1998 (Article)
DOI: 10.1021/jo980134j

Optimization and Mechanistic Analysis of Oligonucleotide Cleavage from Palladium-Labile Solid-Phase Synthesis Supports1

Marc M. Greenberg, Tracy J. Matray, Jeffrey D. Kahl, Dong Jin Yoo, and Dustin L. McMinn
pp 4062–4068
Publication Date (Web): May 27, 1998 (Article)
DOI: 10.1021/jo980135b

Enantiospecific Synthesis of Natural (−)-Cocaine and Unnatural (+)-Cocaine from d- and l-Glutamic Acid

Ronghui Lin, Josep Castells, and Henry Rapoport
pp 4069–4078
Publication Date (Web): May 15, 1998 (Article)
DOI: 10.1021/jo980153t

Design, Synthesis, and Self-Assembly of “Artificial Dinucleotide Duplexes”

Jonathan L. Sessler and Ruizheng Wang
pp 4079–4091
Publication Date (Web): May 21, 1998 (Article)
DOI: 10.1021/jo980194p

Effects of Polymer Supports on the Kinetics of Solid-Phase Organic Reactions:  A Comparison of Polystyrene- and TentaGel-Based Resins

Wenbao Li and Bing Yan
pp 4092–4097
Publication Date (Web): May 28, 1998 (Article)
DOI: 10.1021/jo9802271

The Total Synthesis of Tritiated and Deuterated 5-Oxo-ETE, a Novel Inflammatory Mediator

Subhash P. Khanapure, Xiao-Xin Shi, William S. Powell, and Joshua Rokach
pp 4098–4102
Publication Date (Web): May 19, 1998 (Article)
DOI: 10.1021/jo980280p

Templation in the Formation of Carceplexes

Robert G. Chapman and John C. Sherman
pp 4103–4110
Publication Date (Web): May 15, 1998 (Article)
DOI: 10.1021/jo9803582

A Concise Route to 19-Nor-10-azasteroids, a New Class of Steroid 5α-Reductase Inhibitors. 3.1 Synthesis of (+)-19-Nor-10-azatestosterone and (+)-17β-(Acetyloxy)-(5β)-10-azaestr-1-en-3-one

Antonio Guarna, Ernesto G. Occhiato, Fabrizio Machetti, and Dina Scarpi
pp 4111–4115
Publication Date (Web): May 14, 1998 (Note)
DOI: 10.1021/jo971917s

Synthesis of 1,2,3,4-Tetrahydroisoquinolines Containing Electron-Withdrawing Groups

George J. Quallich, Teresa W. Makowski, Andrew F. Sanders, Frank J. Urban, and Enrique Vazquez
pp 4116–4119
Publication Date (Web): May 19, 1998 (Note)
DOI: 10.1021/jo972184e

Asymmetric Allylation and Reduction on an Ephedrine-Derived Template:  Stereoselective Synthesis of α-Hydroxy Acids and Derivatives

Sunil V. Pansare, R. Gnana Ravi, and Rajendra P. Jain
pp 4120–4124
Publication Date (Web): May 15, 1998 (Note)
DOI: 10.1021/jo9722820

One-Pot Synthesis of α-Amino Phosphonates from Aldehydes Using Lanthanide Triflate as a Catalyst

Changtao Qian and Taisheng Huang
pp 4125–4128
Publication Date (Web): May 22, 1998 (Note)
DOI: 10.1021/jo971242t

Facile Oxidation of Silyl Enol Ethers with Hydrogen Peroxide Catalyzed by Methyltrioxorhenium

Saša Stanković and James H. Espenson
pp 4129–4130
Publication Date (Web): May 21, 1998 (Note)
DOI: 10.1021/jo972315b

Tandem Reductive Alkylation−Cyclization for the Preparation of Unsymmetrical 1,4-Disubstituted 2,3-Diketopiperazines

Christopher J. Dinsmore and Jeffrey M. Bergman
pp 4131–4134
Publication Date (Web): May 21, 1998 (Note)
DOI: 10.1021/jo9800309

Tetraenylstannanes in the Synthesis of Retinoic Acid and Its Ring-Modified Analogues

Beatriz Domínguez, Beatriz Iglesias, and Angel R. de Lera
pp 4135–4139
Publication Date (Web): May 15, 1998 (Note)
DOI: 10.1021/jo980097w

Transition-Metal-Catalyzed Oxidations. 11.1 Total Synthesis of (±)-Lacinilene C Methyl Ether by β-Naphthol to α-Ketol Oxidation

Karsten Krohn and Gregor Zimmermann
pp 4140–4142
Publication Date (Web): May 22, 1998 (Note)
DOI: 10.1021/jo9801566

Lewis Acid Catalyzed Diels−Alder Reactions of Highly Hindered Dienophiles

Robert D. Hubbard and Benjamin L. Miller
pp 4143–4146
Publication Date (Web): May 20, 1998 (Note)
DOI: 10.1021/jo9801667

Cadiolides A and B, New Metabolites from an Ascidian of the Genus Botryllus

Cameron J. Smith, Robert L. Hettich, Jamaluddin Jompa, Akbar Tahir, Michelle V. Buchanan, and Chris M. Ireland
pp 4147–4150
Publication Date (Web): May 21, 1998 (Note)
DOI: 10.1021/jo980171a

Doubly Diastereocontrolled Cyclization Based on Intramolecular Conjugate Addition Reactions Involving an Allylic Radical and an Anion

Takashi Tokoroyama and Takehiko Aoto
pp 4151–4157
Publication Date (Web): May 27, 1998 (Note)
DOI: 10.1021/jo980188t

Heck Arylation of 1,2-Cyclohexanedione and 2-Ethoxy-2-cyclohexenone

Neeraj Garg, Mats Larhed, and Anders Hallberg
pp 4158–4162
Publication Date (Web): May 21, 1998 (Note)
DOI: 10.1021/jo980221b
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