Table of Contents

September 17, 1999
Volume 64, Issue 19
Pages 6937-7280
For Selected Content:

Articles

Electron Acceptors of the Fluorene Series. 9.1 Derivatives of 9-(1,2-Dithiol-3-ylidene)-, 9-(1,3-Dithiol-2-ylidene)-, and 9-(1,3-Selenathiol-2-ylidene)fluorenes:  Synthesis, Intramolecular Charge Transfer, and Redox Properties

Dmitrii D. Mysyk, Igor F. Perepichka, Dmitrii F. Perepichka, Martin R. Bryce, Anatolii F. Popov, Leonid M. Goldenberg, and Adrian J. Moore
pp 6937–6950
Publication Date (Web): August 25, 1999 (Article)
DOI: 10.1021/jo990100r

Radical Cations of Trialkylamines:  ESR Spectra and Structures

Armin de Meijere, Vladimir Chaplinski, Fabian Gerson, Pascal Merstetter, and Edwin Haselbach
pp 6951–6959
Publication Date (Web): August 25, 1999 (Article)
DOI: 10.1021/jo990458n

Rate Constants for 5-Exo Secondary Alkyl Radical Cyclizations onto Hydrazones and Oxime Ethers via Intramolecular Competition Experiments

Poonam Tauh and Alex G. Fallis
pp 6960–6968
Publication Date (Web): August 25, 1999 (Article)
DOI: 10.1021/jo982017u

Poly Methoxy Phenols in Solution:  O−H Bond Dissociation Enthalpies, Structures, and Hydrogen Bonding

Martine I. de Heer, Hans-Gert Korth, and Peter Mulder
pp 6969–6975
Publication Date (Web): September 01, 1999 (Article)
DOI: 10.1021/jo9901485

Resveratrol Tetramers from Vatica diospyroides

Eun-Kyoung Seo, Heebyung Chai, Howard L. Constant, Thawatchai Santisuk, Vichai Reutrakul, Christopher W. W. Beecher, Norman R. Farnsworth, Geoffrey A. Cordell, John M. Pezzuto, and A. Douglas Kinghorn
pp 6976–6983
Publication Date (Web): August 25, 1999 (Article)
DOI: 10.1021/jo9902087

2-Chloro-1,3-dimethylimidazolinium Chloride. 1. A Powerful Dehydrating Equivalent to DCC

Toshio IsobeTsutomu Ishikawa
pp 6984–6988
Publication Date (Web): August 24, 1999 (Article)
DOI: 10.1021/jo990210y

2-Chloro-1,3-dimethylimidazolinium Chloride. 2. Its Application to the Construction of Heterocycles through Dehydration Reactions

Toshio IsobeTsutomu Ishikawa
pp 6989–6992
Publication Date (Web): August 24, 1999 (Article)
DOI: 10.1021/jo9909756

Novel Camphor-Derived Chiral Auxiliaries:  Significant Solvent and Additive Effects on Asymmetric Reduction of Chiral α-Keto Esters

Ying-Yuan Chu, Chia-Sheng Yu, Chiou-Juy Chen, Kung-Shuo Yang, Jung-Chaing Lain, Chun-Hui Lin, and Kwunmin Chen
pp 6993–6998
Publication Date (Web): August 25, 1999 (Article)
DOI: 10.1021/jo9902188

Self-Assembly of 3-[4‘-(Diethylboryl)phenyl]pyridine and 3-[3‘-(Diethylboryl)phenyl]pyridine:  Synthesis, Structural Features, and Stability in Solution

Shigeharu Wakabayashi, Yoshikazu Sugihara, Katsuto Takakura, Shigeru Murata, Hideo Tomioka, Shiho Ohnishi, and Kazuyuki Tatsumi
pp 6999–7008
Publication Date (Web): September 1, 1999 (Article)
DOI: 10.1021/jo981632v

Porphyrin Clips Derived from Diphenylglycoluril. Synthesis, Conformational Analysis, and Binding Properties

Johannes A. A. W. Elemans, Menno B. Claase, Patrick P. M. Aarts, Alan E. Rowan, Albertus P. H. J. Schenning, and Roeland J. M. Nolte
pp 7009–7016
Publication Date (Web): September 1, 1999 (Article)
DOI: 10.1021/jo990112c

Dephosphonylation of β-Carbonyl Phosphonates

Shi Yong Lee, Chi-Wan Lee, and Dong Young Oh
pp 7017–7022
Publication Date (Web): August 21, 1999 (Article)
DOI: 10.1021/jo990221r

Novel C19 Homolignans, Taiwanschirin A, B, and Cytotoxic Taiwanschirin C, and a New C18 Lignan, Schizanrin A, from Schizandra arisanensis

Yao-Haur Kuo, Hui-Chi Huang, Li-Ming Yang Kuo, andLi-Ming Yang Kuo, and Chieh-Fu Chen
pp 7023–7027
Publication Date (Web): August 31, 1999 (Article)
DOI: 10.1021/jo990263f

Photoinduced Single Electron Transfer on 5-Aryl-1,2,4-oxadiazoles:  Some Mechanistic Investigations in the Synthesis of Quinazolin-4-ones

Silvestre Buscemi, Andrea Pace, and Nicolò VivonaTullio CaronnaAlessandro Galia
pp 7028–7033
Publication Date (Web): August 31, 1999 (Article)
DOI: 10.1021/jo990298f

Synthesis and Solution Structure Analysis of a Bispyrenyl Bishydroxamate Calix[4]arene-Based Receptor, a Fluorescent Chemosensor for Cu2+ and Ni2+ Metal Ions

Bruno Bodenant, Tanja Weil, Magali Businelli-Pourcel, Frédéric Fages, Bernard Barbe, Isabelle Pianet, and Michel Laguerre
pp 7034–7039
Publication Date (Web): August 25, 1999 (Article)
DOI: 10.1021/jo9904720

Cis and Enantioselective Synthesis of 2-Oxazoline-4-carboxylates through Lewis Acid-Catalyzed Formal [3 + 2] Cycloaddition of 5-Alkoxyoxazoles with Aldehydes

Hiroyuki Suga, Kosei Ikai, and Toshikazu Ibata
pp 7040–7047
Publication Date (Web): August 25, 1999 (Article)
DOI: 10.1021/jo990525d

Bis(2-methoxyethyl)aminosulfur Trifluoride:  A New Broad-Spectrum Deoxofluorinating Agent with Enhanced Thermal Stability

Gauri S. Lal, Guido P. Pez, Reno J. Pesaresi, Frank M. Prozonic, and Hansong Cheng
pp 7048–7054
Publication Date (Web): August 21, 1999 (Article)
DOI: 10.1021/jo990566+

Ionic Effects on the Stereoselectivities of Diels−Alder Reactions:  The Cyclopentadiene−Methyl Acrylate Reaction in Aqueous LiCl, NaCl, NaBr, CaCl2, LiClO4, and Guanidinium Chloride

Sanjay S. Pawar, Usha Phalgune, and Anil Kumar
pp 7055–7060
Publication Date (Web): August 31, 1999 (Article)
DOI: 10.1021/jo990583z

A Hard−Soft Acid−Base and DFT Analysis of Singlet−Triplet Gaps and the Addition of Singlet Carbenes to Alkenes

Francisco Mendez and Miguel A. Garcia-Garibay
pp 7061–7066
Publication Date (Web): August 25, 1999 (Article)
DOI: 10.1021/jo990584r

Total Synthesis of Squamotacin

Santosh C. Sinha, Subhash C. Sinha, and Ehud Keinan
pp 7067–7073
Publication Date (Web): August 21, 1999 (Article)
DOI: 10.1021/jo990599p

Preparation and Properties of 2-Methyleneoxetanes

Lisa M. Dollinger, Albert J. Ndakala, Mehrnoosh Hashemzadeh, Gan Wang, Ying Wang, Isamir Martinez, Joel T. Arcari, David J. Galluzzo, and Amy R. HowellArnold L. Rheingold and Joshua S. Figuero
pp 7074–7080
Publication Date (Web): August 21, 1999 (Article)
DOI: 10.1021/jo9906072

Cyclization Reactions of Nucleoside Anomeric Radical with Olefin Tethered on Base:  Factors That Induce Anomeric Stereochemistry

Atsushi Kittaka, Takashi Asakura, Tetsuya Kuze, Hiromichi Tanaka, Naoki Yamada, Kazuo T. Nakamura, and Tadashi Miyasaka
pp 7081–7093
Publication Date (Web): August 21, 1999 (Article)
DOI: 10.1021/jo990611d

Convergent Solution-Phase Combinatorial Synthesis with Multiplication of Diversity through Rigid Biaryl and Diarylacetylene Couplings

Dale L. Boger, Weiqin Jiang, and Joel Goldberg
pp 7094–7100
Publication Date (Web): August 21, 1999 (Article)
DOI: 10.1021/jo990639p

Total Synthesis of C-Glycosylangucycline, Urdamycinone B, Using an Unprotected Sugar

Goh Matsuo, Yuko Miki, Masaya Nakata, Shuichi Matsumura, and Kazunobu Toshima
pp 7101–7106
Publication Date (Web): August 21, 1999 (Article)
DOI: 10.1021/jo990648y

Supramolecular Aggregation of m-Nitrobenzoic Acid by C−H···O and O−H···O Hydrogen Bondings in the Crystalline Charge-Transfer Complexes with Aromatic Hydrocarbons

Takanori Suzuki and Takashi TsujiTakanori Fukushima, Setsuko Miyanari, and Tsutomu MiyashiYasuyuki Sakata, Tsutomu Kouda, and Hiroki Kamiyama
pp 7107–7113
Publication Date (Web): August 25, 1999 (Article)
DOI: 10.1021/jo990658z

Solid-Phase Strategies for the Assembly of Template-Based Protein Mimetics1

Stéphane Peluso, Pascal Dumy, Céline Nkubana, Yoshihiro Yokokawa, and Manfred Mutter
pp 7114–7120
Publication Date (Web): August 31, 1999 (Article)
DOI: 10.1021/jo990669s

Reactions of Nitrosonium Ethyl Sulfate with Olefins and Dienes:  An Experimental and Theoretical Study

Nikolai V. Zyk, Evgueni E. Nesterov, Andrei N. Khlobystov, and Nikolai S. ZefirovLoren A. Barnhurst and Andrei G. Kutateladze
pp 7121–7128
Publication Date (Web): August 31, 1999 (Article)
DOI: 10.1021/jo990679t

High-Spin Polyphenoxyl Based on Poly(1,4-phenyleneethynylene)

Hiroyuki Nishide, Tadatoshi Maeda, Kenichi Oyaizu, and Eishun Tsuchida
pp 7129–7134
Publication Date (Web): August 31, 1999 (Article)
DOI: 10.1021/jo990691l

2-Naphthalenesulfonyl as a Tosyl Substitute for Protection of Amino Functions. Cyclic Voltammetry Studies on Model Sulfonamides and Their Preparative Cleavage by Reduction

Barthélémy Nyasse, Leif Grehn, Hernani L. S. Maia, Luis S. Monteiro, and Ulf Ragnarsson
pp 7135–7139
Publication Date (Web): August 31, 1999 (Article)
DOI: 10.1021/jo990695q

Synthesis, Reactions, and Structural and NMR Features of [2.2]Metacyclophane Monoenes and Their Tricarbonylchromium and Cyclopentadienyliron(+) Complexes

Reginald H. Mitchell and Limin Zhang
pp 7140–7152
Publication Date (Web): August 31, 1999 (Article)
DOI: 10.1021/jo990721k

A One-Pot Method for the Stereoselective Introduction of a Vinyl Group via an Atom-Transfer Radical-Cyclization Reaction with a Diphenylvinylsilyl Group as a Temporary Connecting Tether. Synthesis of 4‘α-C-Vinylthymidine, a Potent Antiviral Nucleoside1

Isamu Sugimoto, Satoshi Shuto, and Akira Matsuda
pp 7153–7157
Publication Date (Web): August 21, 1999 (Article)
DOI: 10.1021/jo990787f

Nucleosides and Nucleotides. 184. Synthesis and Conformational Investigation of Anti-Fixed 3-Deaza-3-halopurine Ribonucleosides1,2

Noriaki Minakawa, Naoshi Kojima, and Akira Matsuda
pp 7158–7172
Publication Date (Web): August 31, 1999 (Article)
DOI: 10.1021/jo990638x

Nitro Compounds in the Double Annulation Route to Trans-Fused Bicyclic Compounds

Robert B. Grossman, Ravindra M. Rasne, and Brian O. Patrick
pp 7173–7177
Publication Date (Web): August 31, 1999 (Article)
DOI: 10.1021/jo9907888

[n + 1] Annulation Route to Highly Substituted Cyclic Ketones with Pendant Ketone, Nitrile, and Ester Functionality

Robert B. Grossman, Dhananjay S. Pendharkar, and Brian O. Patrick
pp 7178–7183
Publication Date (Web): August 31, 1999 (Article)
DOI: 10.1021/jo9907787

Total Synthesis of Michellamines A−C, Korupensamines A−D, and Ancistrobrevine B

Thomas R. Hoye, Minzhang Chen, Bac Hoang, Liang Mi, and Owen P. Priest
pp 7184–7201
Publication Date (Web): August 24, 1999 (Article)
DOI: 10.1021/jo9908187

Ruthenium Carbene-Based Olefin Metathesis Initiators:  Catalyst Decomposition and Longevity

Michael Ulman and Robert H. Grubbs
pp 7202–7207
Publication Date (Web): September 1, 1999 (Article)
DOI: 10.1021/jo9908703

Daphnezomines A and B, Novel Alkaloids with an Aza-adamantane Core from Daphniphyllum humile

Hiroshi Morita, Naotoshi Yoshida, and Jun'ichi Kobayashi
pp 7208–7212
Publication Date (Web): August 21, 1999 (Article)
DOI: 10.1021/jo990882o

Enantioselective Synthesis of 12-epi-PGF2α and 12,15-diepi-PGF2α

Sheng Lai, Dongreyoul Lee, Jong Sun U, and Jin Kun Cha
pp 7213–7217
Publication Date (Web): August 25, 1999 (Article)
DOI: 10.1021/jo990906r

On the Reaction of Tryptophan Derivatives with N-Phenylselenyl Phthalimide:  The Nature of the Kinetic and Thermodynamic Hexahydropyrrolo[2,3-b]indole Products. Alkylation of Tryptophan with Inversion of Configuration

David Crich and Xianhai Huang
pp 7218–7223
Publication Date (Web): August 18, 1999 (Article)
DOI: 10.1021/jo991093+

Conformational Properties of Epothilone

Richard E. Taylor and Jaroslav Zajicek
pp 7224–7228
Publication Date (Web): August 25, 1999 (Article)
DOI: 10.1021/jo991014u

Notes

A New Route to Cross-Conjugated Bis(enamines) and an Unusual Reaction with DDQ

Teresa M. V. D. Pinho e Melo, Ana M. T. D. P. V. Cabral, Antnio M. d'A. Rocha Gonsalves, Ana M. Beja, José A. Paixão, Manuela R. Silva, and Luiz Alte da VeigaThomas L. Gilchrist
pp 7229–7232
Publication Date (Web): August 21, 1999 (Note)
DOI: 10.1021/jo9901384

Synthesis and Stereochemistry of 11,11a-Dihydro Derivatives of (4S)-2,4-Dimethyl-2,4-dihydro-1H- pyrazino[2,1-b]quinazoline-3,6-diones. A New Transannular Rearrangement Proposal

Sonsoles Martín-Santamaría, Modesta Espada, and Carmen Avendaño
pp 7233–7235
Publication Date (Web): August 21, 1999 (Note)
DOI: 10.1021/jo981957b

How Selective Threading of Amides through Macrocylic Lactam Wheels Leads to Rotaxane Synthesis

Christian Seel, Amir H. Parham, Oliver Safarowsky, Gosia M. Hübner, and Fritz Vögtle
pp 7236–7242
Publication Date (Web): August 21, 1999 (Note)
DOI: 10.1021/jo990042+

Inexpensive and Environmentally Friendly Oxidation of Hydroxylamines to Nitrones with Bleach

Stefano Cicchi, Massimo Corsi, and Andrea Goti
pp 7243–7245
Publication Date (Web): August 21, 1999 (Note)
DOI: 10.1021/jo990417r

Synthesis of Small-Sized Stilbenophanes and Their Transannular Delocalization

Akihiko Tsuge, Toshihiro Nishimoto, Tomoko Uchida, Mikio Yasutake, Tetsuji Moriguchi, and Kazunori Sakata
pp 7246–7248
Publication Date (Web): August 31, 1999 (Note)
DOI: 10.1021/jo990488q

Structural and Chemical Properties of 3,10-Diaza-N,N-dimethyldispiro[5.0.5.3]- pentadeca-1,4,8,11-tetraene:  A Novel Heterocyclic Dispiro Compound

Takashi Muramatsu, Azumao Toyota, Mikako Kudou, Yusaku Ikegami, and Masataka Watanabe
pp 7249–7253
Publication Date (Web): September 1, 1999 (Note)
DOI: 10.1021/jo990514k

Synthesis of a Versatile Neuraminic Acid “C”-Disaccharide Precursor for the Synthesis of C-Glycoside Analogues of Gangliosides

Hélène G. Bazin, Yuguo Du, Tülay Polat, and Robert J. Linhardt
pp 7254–7259
Publication Date (Web): September 1, 1999 (Note)
DOI: 10.1021/jo990564p

Diels−Alder Cycloaddition of 11-Oxapentacyclo[6.5.2.23,6.02,7.09,13]- heptadeca-4,14,16-triene-4,5-dicarboxylic Anhydride with Cyclopentadiene and the Transannular Reactions of the Resulting Cycloadducts

Cheng-Tung Lin, Hsiang-Chin Hsu, and Teh-Chang Chou
pp 7260–7264
Publication Date (Web): August 24, 1999 (Note)
DOI: 10.1021/jo990569m

Highly Efficient Glycosylation of Sapogenins

Shaojiang Deng, Biao Yu, Jianming Xie, and Yongzheng Hui
pp 7265–7266
Publication Date (Web): August 31, 1999 (Note)
DOI: 10.1021/jo990603x

A Heterogeneous Tungsten Catalyst for Epoxidation of Terpenes and Tungsten-Catalyzed Synthesis of Acid-Sensitive Terpene Epoxides

Aída L. Villa de P., Bert F. Sels, Dirk E. De Vos, and Pierre A. Jacobs
pp 7267–7270
Publication Date (Web): August 31, 1999 (Note)
DOI: 10.1021/jo990790z

Anomalous Products from Intramolecular C−H Insertion by a Rhodium Carbenoid. Possible Involvement of a Zwitterionic Mechanism

James D. White and Peter Hrnciar
pp 7271–7273
Publication Date (Web): September 1, 1999 (Note)
DOI: 10.1021/jo990797g

The First Chiral Solvating Agent (CSA) without 1H NMR Signals:  the Perdeuterio- 2,2,2-trifluoro-1-(9-anthryl)ethanol. Preparation and Chiral Induction on Protonated Pirkle Alcohol

Juan Gil and Albert Virgili
pp 7274–7276
Publication Date (Web): August 21, 1999 (Note)
DOI: 10.1021/jo990917k

A Practical Route to Multifunctional 2-Azido-2-deoxy-d-glucopyranosyl Donors

Vince Pozsgay
pp 7277–7280
Publication Date (Web): August 31, 1999 (Note)
DOI: 10.1021/jo990811p

Additions and Corrections

Regio- and Stereocontrolled 6-Endo-Trig Radical Cyclization of Vinyl Radicals:  A Novel Entry to Carbasugars from Carbohydrates.

Ana M. Gomez, Gerardo O. Danelón, Serafín Valverde, and J. Cristóbal López.
p 7280
Publication Date (Web): August 31, 1999 (Addition/Correction)
DOI: 10.1021/jo994005u
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