Table of Contents

May 19, 2000
Volume 65, Issue 10
Pages 2851-3258
For Selected Content:

Articles

Hybrid Anthracyclines from a Genetically Engineered Streptomyces galilaeus Mutant

Tero J. Kunnari, Kristiina P. J. Ylihonko, Karel D. Klika, Pekka I. Mäntsälä, and Juha M. L. Hakala
pp 2851–2855
Publication Date (Web): April 14, 2000 (Article)
DOI: 10.1021/jo980345o

Additions of Enantiopure α-Sulfinyl Carbanions to (S)-N-Sulfinimines:  Asymmetric Synthesis of β-Amino Sulfoxides and β-Αmino Alcohols

José L. García Ruano, Ana Alcudia, Miriam del Prado, David Barros, M. Carmen Maestro, and Inmaculada Fernández
pp 2856–2862
Publication Date (Web): April 25, 2000 (Article)
DOI: 10.1021/jo9903858

Further Studies of the Thermal and Photochemical Diels−Alder Reactions of N-Methyl-1,2,4-triazoline-3,5-dione (MeTAD) with Naphthalene and Some Substituted Naphthalenes

Gary W. Breton and Kristy A. Newton
pp 2863–2869
Publication Date (Web): April 27, 2000 (Article)
DOI: 10.1021/jo9906429

Molecular Design of Crown Ethers. 19.1 Synthesis of Novel Disulfide- and Diselenide-Bridged Bis(benzo-12-crown-4)s and Their Ag+-Selective Electrode Properties

Yu Liu, Heng-Yi Zhang, Lang-Xing Chen, Xi-Wen He, Takehiko Wada, and Yoshihisa Inoue
pp 2870–2874
Publication Date (Web): April 27, 2000 (Article)
DOI: 10.1021/jo991142i

Synthesis of (+)-Casuarine

Scott E. Denmark and Alexander R. Hurd
pp 2875–2886
Publication Date (Web): April 21, 2000 (Article)
DOI: 10.1021/jo991680v

Synthesis of (−)-7-Epiaustraline and (−)-1-Epicastanospermine

Scott E. Denmark and B. Herbert
pp 2887–2896
Publication Date (Web): March 23, 2000 (Article)
DOI: 10.1021/jo991990d

NaY Zeolite as Host for the Selective Heterogeneous Oxidation of Silanes and Olefins with Hydrogen Peroxide Catalyzed by Methyltrioxorhenium

Waldemar Adam, Chantu R. Saha-Möller, and Oliver Weichold
pp 2897–2899
Publication Date (Web): April 14, 2000 (Article)
DOI: 10.1021/jo991908e

4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) Dyes Modified for Extended Conjugation and Restricted Bond Rotations

Jiong Chen, Armin Burghart, Agnes Derecskei-Kovacs, and Kevin Burgess
pp 2900–2906
Publication Date (Web): April 18, 2000 (Article)
DOI: 10.1021/jo991927o

Engineering Acyclic Stereocontrol in the Alkylation of Vinylglycine-Derived Dianions:  Asymmetric Synthesis of Higher α-Vinyl Amino Acids

David B. Berkowitz, Jill M. McFadden, and Marianne K. Sloss
pp 2907–2918
Publication Date (Web): April 19, 2000 (Article)
DOI: 10.1021/jo9918091

Thermal Isomerizations of Ketenimines to Nitriles:  Evaluations of Sigma-Dot (σ•) Constants for Spin-Delocalizations

Sung Soo Kim, Yu Zhu, and Kwang Ho Lee
pp 2919–2923
Publication Date (Web): April 26, 2000 (Article)
DOI: 10.1021/jo991186r

Studies on the Synthetic Compatibility of Aryloxime Linkers in the Solid-Phase Synthesis of 3-Aminobenzisoxazoles

Salvatore D. Lepore and Michael R. Wiley
pp 2924–2932
Publication Date (Web): April 22, 2000 (Article)
DOI: 10.1021/jo991263i

Synthesis and Characterization of Pyridine-Based Polyamido-Polyester Optically Active Macrocycles and Enantiomeric Recognition for d- and l-Amino Acid Methyl Ester Hydrochloride

Hongwu Zhao and Wenting Hua
pp 2933–2938
Publication Date (Web): April 19, 2000 (Article)
DOI: 10.1021/jo9913715

Glucose-Derived 3‘-(Carboxymethyl)-3‘-deoxyribonucleosides and 2‘,3‘-Lactones as Synthetic Precursors for Amide-Linked Oligonucleotide Analogues1

Morris J. Robins, Bogdan Doboszewski, Victor A. Timoshchuk, and Matt A. Peterson
pp 2939–2945
Publication Date (Web): April 21, 2000 (Article)
DOI: 10.1021/jo991399g

Quantitative Monitoring of Solid Phase Organic Reactions by High-Resolution Magic Angle Spinning NMR Spectroscopy

Ralf Warrass and Guy Lippens
pp 2946–2950
Publication Date (Web): April 14, 2000 (Article)
DOI: 10.1021/jo9914824

Total Synthesis of Cyclosporin O Both in Solution and in the Solid Phase Using Novel Thiazolium-, Immonium-, and Pyridinium-Type Coupling Reagents:  BEMT, BDMP, and BEP1

Peng Li and Jie Cheng Xu
pp 2951–2958
Publication Date (Web): April 21, 2000 (Article)
DOI: 10.1021/jo991687c

Chemical Synthesis of Cross-Link Lesions Found in Nitrous Acid Treated DNA:  A General Method for the Preparation of N2-Substituted 2‘-Deoxyguanosines

Eric A. Harwood, Paul B. Hopkins, and Snorri Th. Sigurdsson
pp 2959–2964
Publication Date (Web): April 20, 2000 (Article)
DOI: 10.1021/jo991501+

The “Non-Oxidative” Pummerer Reaction:  Conclusive Evidence for SN2-Type Stereoselectivity, Mechanistic Insight, and Synthesis of Enantiopure l-α-Trifluoromethylthreoninate and d-α-Trifluoromethyl-allo-threoninate1

Marcello Crucianelli, Pierfrancesco Bravo, Alberto Arnone, Eleonora Corradi, Stefano V. Meille, and Matteo Zanda
pp 2965–2971
Publication Date (Web): April 15, 2000 (Article)
DOI: 10.1021/jo991534p

NO2+ Nitration Mechanism of Aromatic Compounds:  Electrophilic vs Charge-Transfer Process

Mutsuo Tanaka, Eiko Muro, Hisanori Ando, Qiang Xu, Masahiro Fujiwara, Yoshie Souma, and Yoichi Yamaguchi
pp 2972–2978
Publication Date (Web): April 26, 2000 (Article)
DOI: 10.1021/jo991538u

Catalytic Enantioselective Protonation of Lithium Enolates with Chiral Imides

Akira Yanagisawa, Tsuyoshi Watanabe, Tetsuo Kikuchi, and Hisashi Yamamoto
pp 2979–2983
Publication Date (Web): April 27, 2000 (Article)
DOI: 10.1021/jo991565k

Direct Transformations of Ketones to γ-Unsaturated Thiols via [2,3]-Sigmatropic Rearrangement of Allyl Sulfinyl Carbanions:  A Combined Experimental and Computational Study

Andrey A. Fokin, Andrey O. Kushko, Anton V. Kirij, Alexander G. Yurchenko, and Paul v. R. Schleyer
pp 2984–2995
Publication Date (Web): April 14, 2000 (Article)
DOI: 10.1021/jo991672e

Olefin Epoxidation by Peroxo Complexes of Cr, Mo, and W. A Comparative Density Functional Study

Cristiana Di Valentin, Philip Gisdakis, Ilya V. Yudanov, and Notker Rösch
pp 2996–3004
Publication Date (Web): April 20, 2000 (Article)
DOI: 10.1021/jo9916784

Halogenations of Anthracenes and Dibenz[a,c]anthracene with N-Bromosuccinimide and N-Chlorosuccinimide1

Shaoming Duan, Jeff Turk, Joseph Speigle, Jean Corbin, John Masnovi, and Ronald J. Baker
pp 3005–3009
Publication Date (Web): April 26, 2000 (Article)
DOI: 10.1021/jo991495h

Aminosulf(ox)ides as Ligands for Iridium(I)-Catalyzed Asymmetric Transfer Hydrogenation

Daniëlle G. I. Petra, Paul C. J. Kamer, Anthony L. Spek, Hans E. Schoemaker, and Piet W. N. M. van Leeuwen
pp 3010–3017
Publication Date (Web): April 14, 2000 (Article)
DOI: 10.1021/jo991700t

Asymmetric and Nonasymmetric Addition of RLi and RMgX to 3-Methoxynaphthalen-2-yl Oxazolines and Imines. An Approach to Substituted 2-Tetralones

Sergei V. Kolotuchin and A. I. Meyers
pp 3018–3026
Publication Date (Web): April 26, 2000 (Article)
DOI: 10.1021/jo991727c

Design and Synthesis of a Transferable Farnesyl Pyrophosphate Analogue to Ras by Protein Farnesyltransferase

Kareem A. H. Chehade, Douglas A. Andres, Hiromi Morimoto, and H. Peter Spielmann
pp 3027–3033
Publication Date (Web): April 14, 2000 (Article)
DOI: 10.1021/jo991735t

New Chiral Didehydroamino Acid Derivatives from a Cyclic Glycine Template with 3,6-Dihydro-2H-1,4-oxazin-2-one Structure:  Applications to the Asymmetric Synthesis of Nonproteinogenic α-Amino Acids

Rafael Chinchilla, Larry R. Falvello, Nuria Galindo, and Carmen Nájera
pp 3034–3041
Publication Date (Web): April 19, 2000 (Article)
DOI: 10.1021/jo991736l

Synthesis of Functionalized Chiral Carbocyclic Cleft Molecules Complementary to Tröger's Base Derivatives

Marc C. Kimber, Andrew C. Try, Leoni Painter, Margaret M. Harding, and Peter Turner
pp 3042–3046
Publication Date (Web): April 22, 2000 (Article)
DOI: 10.1021/jo991741p

Effect of Chain Length and Ring Size of Alkyl and Cycloalkyl Side-Chain Substituents upon the Biological Activity of Brassinosteroids. Preparation of Novel Analogues with Activity Exceeding that of Brassinolide

Thomas G. Back, Loeke Janzen, Suanne K. Nakajima, and Richard P. Pharis
pp 3047–3052
Publication Date (Web): April 18, 2000 (Article)
DOI: 10.1021/jo9917947

Electron Acceptors of the Fluorene Series. 10.1 Novel Acceptors Containing Butylsulfanyl, Butylsulfinyl, and Butylsulfonyl Substituents:  Synthesis, Cyclic Voltammetry, Charge-Transfer Complexation with Anthracene in Solution, and X-ray Crystal Structures of Two Tetrathiafulvalene Complexes

Igor F. Perepichka, Anatolii F. Popov, Tatyana V. Orekhova, Martin R. Bryce, Alexander M. Andrievskii, Andrei S. Batsanov, Judith A. K. Howard, and Nikolai I. Sokolov
pp 3053–3063
Publication Date (Web): April 26, 2000 (Article)
DOI: 10.1021/jo991796r

Efficient Synthesis of 3,6-Dideoxy-β-d-arabino-hexopyranosyl-Terminated LacdiNac Glycan Chains of the Trichinella spiralis Parasite

Mark Nitz and David R. Bundle
pp 3064–3073
Publication Date (Web): April 20, 2000 (Article)
DOI: 10.1021/jo991812k

Synthesis of Enantiopure trans-3,4-Disubstituted Piperidines. An Enantiodivergent Synthesis of (+)- and (−)-Paroxetine

Mercedes Amat, Joan Bosch, José Hidalgo, Margalida Cantó, Maria Pérez, Núria Llor, Elies Molins, Carles Miravitlles, Modesto Orozco, and Javier Luque
pp 3074–3084
Publication Date (Web): April 20, 2000 (Article)
DOI: 10.1021/jo991816p

Synthesis and Reactions of (E)- and (Z)-1,3-Dibromo-2-methoxypropene

Kjetil Røe Edvardsen and Tore BennecheMarcus A. Tius
pp 3085–3089
Publication Date (Web): April 13, 2000 (Article)
DOI: 10.1021/jo991822l

Studies on the Mechanism of B(C6F5)3-Catalyzed Hydrosilation of Carbonyl Functions

Daniel J. Parks, James M. Blackwell, and Warren E. Piers
pp 3090–3098
Publication Date (Web): April 20, 2000 (Article)
DOI: 10.1021/jo991828a

Cyclization into Hydrindanones Using Samarium Diiodide

Masakazu Sono, Yasuyo Nakashiba, Katsuyuki Nakashima, and Motoo Tori
pp 3099–3106
Publication Date (Web): April 25, 2000 (Article)
DOI: 10.1021/jo9918450

Tandem One-Pot Palladium-Catalyzed Reductive and Oxidative Coupling of Benzene and Chlorobenzene

Sudip Mukhopadhyay, Gadi Rothenberg, Diana Gitis, and Yoel Sasson
pp 3107–3110
Publication Date (Web): April 26, 2000 (Article)
DOI: 10.1021/jo991868e

Synthesis and Reactions of a Stable o-Quinoid 10-π-Electron System, Furo[3,4-c]pyridine

Tarun K. Sarkar, Sunil K. Ghosh, and Tahsin J. Chow
pp 3111–3115
Publication Date (Web): April 15, 2000 (Article)
DOI: 10.1021/jo991886w

2-Azanorbornyl Alcohols:  Very Efficient Ligands for Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of Aromatic Ketones

Diego A. Alonso, Sofia J. M. Nordin, Peter Roth, Tibor Tarnai, and Pher G. AnderssonMarc Thommen and Ulrich Pittelkow
pp 3116–3122
Publication Date (Web): April 14, 2000 (Article)
DOI: 10.1021/jo991914a

Base-Promoted in Situ Generation of Methyl Acrylate from Dimethyl 3,3‘-Dithiodipropionate. Application to N-Alkylation of Heterocycles

Pierre Hamel and Mario Girard
pp 3123–3125
Publication Date (Web): April 26, 2000 (Article)
DOI: 10.1021/jo9919207

Synthesis of Soluble Bis-terpyridine Ligands Bearing Ethynylene−Phenylene Spacers

Abderrahim Khatyr and Raymond Ziessel
pp 3126–3134
Publication Date (Web): April 22, 2000 (Article)
DOI: 10.1021/jo9919355

Evaluation of β- and γ-Effects of Group 14 Elements Using Intramolecular Competition

Masanobu Sugawara and Jun-ichi Yoshida
pp 3135–3142
Publication Date (Web): April 26, 2000 (Article)
DOI: 10.1021/jo991977t

Synthesis of Cryptophycin 52 Using the Sharpless Asymmetric Dihydroxylation:  Diol to Epoxide Transformation Optimized for a Base-Sensitive Substrate

Jian Liang, Eric D. Moher, Richard E. Moore, and David W. Hoard
pp 3143–3147
Publication Date (Web): April 12, 2000 (Article)
DOI: 10.1021/jo9919862

A Stereoselective Route to Polysubstituted Tetrahydroquinolines by Benzotriazole-Promoted Condensation of Aliphatic Aldehydes and Aromatic Amines

Sanjay Talukdar, Chao-Tsen Chen, and Jim-Min Fang
pp 3148–3153
Publication Date (Web): April 27, 2000 (Article)
DOI: 10.1021/jo000033x

Axially Chiral Analogues of 4-(Dimethylamino)pyridine:  Novel Catalysts for Nonenzymatic Enantioselective Acylations

Alan C. Spivey, Tomasz Fekner, and Sharon E. Spey
pp 3154–3159
Publication Date (Web): April 18, 2000 (Article)
DOI: 10.1021/jo0000574

Rational Synthesis of Meso-Substituted Chlorin Building Blocks

Jon-Paul Strachan, Donal F. O'Shea, Thiagarajan Balasubramanian, and Jonathan S. Lindsey
pp 3160–3172
Publication Date (Web): April 27, 2000 (Article)
DOI: 10.1021/jo991942t

Enantiospecific Total Synthesis of the Sarpagine Related Indole Alkaloids Talpinine and Talcarpine as Well as the Improved Total Synthesis of Alstonerine and Anhydromacrosalhine-methine via the Asymmetric Pictet−Spengler Reaction

Peng Yu, Tao Wang, Jin Li, and James M. Cook
pp 3173–3191
Publication Date (Web): April 26, 2000 (Article)
DOI: 10.1021/jo000126e

Isolation, Structural Characterization, and Synthesis of a Naturally Occurring Bisfuranopseudopterane Ether:  Biskallolide A. Evidence for a Carbocation Intermediate during the Facile Conversion of Kallolide A and Isokallolide A into Various Solvolysis Products

Abimael D. Rodríguez, Jian-Gong Shi, and Yan-Ping Shi
pp 3192–3199
Publication Date (Web): April 27, 2000 (Article)
DOI: 10.1021/jo0001582

Conformational Studies by Dynamic NMR. 74.1 Stereomutations of the Conformational Enantiomers in Peri-Substituted 1-Acylnaphthalenes

Lodovico Lunazzi, Andrea Mazzanti, and Anna Muñoz Álvarez
pp 3200–3206
Publication Date (Web): April 14, 2000 (Article)
DOI: 10.1021/jo991853g

Notes

Conformational Studies by Dynamic NMR. 73.1 Conformational Enantiomers of Cyclohexene Oxide in the Solid State

Daniele CasariniLodovico Lunazzi and Andrea MazzantiGerald Simon
pp 3207–3208
Publication Date (Web): May 12, 2000 (Note)
DOI: 10.1021/jo991800z

Chiral Nonracemic Synthesis and Reactivity of Two New Endocyclic Enamines in the Phenyloxazolopiperidine Series

David François, Erwan Poupon, Marie-Christine Lallemand, Nicole Kunesch, and Henri-Philippe Husson
pp 3209–3212
Publication Date (Web): April 26, 2000 (Note)
DOI: 10.1021/jo990706f

Simple Asymmetric Synthesis of 2H-Azirines Derived from Phosphine Oxides

Francisco Palacios, Ana Maria Ochoa de Retana, Jose Ignacio Gil, and Jose Maria Ezpeleta
pp 3213–3217
Publication Date (Web): April 14, 2000 (Note)
DOI: 10.1021/jo9915426

Biomimetic-Type Synthesis of Benzo[a]naphthacenequinones Related to Pradimicinone

Karsten Krohn, Sven Bernhard, Ulrich Flörke, and Nasir Hayat
pp 3218–3222
Publication Date (Web): April 20, 2000 (Note)
DOI: 10.1021/jo9918089

Palladium-Catalyzed Reaction of Propargyl Nucleophiles with α-Sulfonyl α,β-Unsaturated Ketones:  A Single-Step Synthesis of Furo[3,4-c] Heterocyclic Derivatives

Nuno Monteiro and Geneviève Balme
pp 3223–3226
Publication Date (Web): April 19, 2000 (Note)
DOI: 10.1021/jo991817h

Total Synthesis of Amaryllidaceae Pyrrolophenanthridinium Alkaloids via the Ziegler−Ullmann Reaction:  Tortuosine, Criasbetaine, and Ungeremine

Lucy M. Stark, Xiao-Fa Lin, and Lee A. Flippin
pp 3227–3230
Publication Date (Web): April 26, 2000 (Note)
DOI: 10.1021/jo991902p

Preparation of a Resin-Bound Arene−Ruthenium Complex and Assessment of Its Use in Enol Formate Synthesis and Olefin Cyclopropanation

Nicholas E. Leadbeater, Kathryn A. Scott, and Lucy J. Scott
pp 3231–3232
Publication Date (Web): April 19, 2000 (Note)
DOI: 10.1021/jo991921z

An Efficient, Stereospecific Synthesis of the Dimer-Selective Retinoid X Receptor Modulator (2E,4E,6Z)-7-[5,6,7,8- Tetrahydro-5,5,8,8-tetramethyl-2- (n-propyloxy)naphthalen-3-yl]-3- methylocta-2,4,6-trienoic Acid

Lawrence G. Hamann
pp 3233–3235
Publication Date (Web): April 13, 2000 (Note)
DOI: 10.1021/jo991936x

Short Total Synthesis of (±)-Galbulin and (±)-Isogalbulin Using Zirconium Chemistry

Alexander N. Kasatkin, Graham Checksfield, and Richard J. Whitby
pp 3236–3238
Publication Date (Web): April 14, 2000 (Note)
DOI: 10.1021/jo9919512

Diiodosilane:  A Reagent for Mild, Efficient Conversion of Carbamates to Ureas via Isocyanates

Stéphane Gastaldi, Steven M. Weinreb, and Didier Stien
pp 3239–3240
Publication Date (Web): April 12, 2000 (Note)
DOI: 10.1021/jo9919714

One-Pot Synthesis of N-Protected Amino Trifluoromethyl Ketones as Hydrated Hydrochloride Salts via the CsF-Catalyzed Reactions of (Trifluoromethyl)trimethylsilane with N-Protected Amino Esters

Rajendra P. Singh and Jean'ne M. Shreeve
pp 3241–3243
Publication Date (Web): April 26, 2000 (Note)
DOI: 10.1021/jo991972w

Rapid Photochemical Generation of Ubiquinol through a Radical Pathway:  An Avenue for Probing Submillisecond Enzyme Kinetics

Brian E. Schultz, Kirk C. Hansen, Charles C. Lin, and Sunney I. Chan
pp 3244–3247
Publication Date (Web): April 26, 2000 (Note)
DOI: 10.1021/jo000028t

Asymmetric Synthesis of (2S,6S)- and meso-(2S,6R)-Diaminopimelic Acids from Enantiopure Bis(sulfinimines)

Franklin A. Davis and Vaidyanathan Srirajan
pp 3248–3251
Publication Date (Web): April 20, 2000 (Note)
DOI: 10.1021/jo000038u

An Oxidative Prins Cyclization Methodology

Chuanfeng Chen and Patrick S. Mariano
pp 3252–3254
Publication Date (Web): April 26, 2000 (Note)
DOI: 10.1021/jo0000832

Double Annulation Route to Highly Substituted and Functionalized cis Bicyclic and Tricyclic δ-Lactams and Imides

Robert B. Grossman, Dhananjay S. Pendharkar, Ravindra M. Rasne, and Melissa A. Varner
pp 3255–3258
Publication Date (Web): April 21, 2000 (Note)
DOI: 10.1021/jo0000978
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