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HETEROCYCLES, Vol. 66, 2005
■ PREFACE
1
Preface
In Memorial Issue of the late Professor Kenji Koga
Shiro Ikegami*
■ CURRICULUM VITAE
3
Biographical Data
Kenji Koga*
■ PUBLICATIONS
7
Original Papers
Kenji Koga*
HETEROCYCLES, Vol. 66, 2005
27
Reviews
Kenji Koga*
■ COMMUNICATIONS
31
Enantioselective Synthesis of (R)-1-Azaspiro[4.4]nonane2,6-dione Ethylene Ketal, Key Chiral Intermediate in the
Elaboration of (-)-Cephalotaxine
Mathieu Pizzonero, Françoise Dumas,* and Jean d’Angelo*
Cephalotaxine
39
Asymmetric Michael Reaction
Curtius Rearrangement
Chiral Enaminoester
Stereoselective Reduction
[2+2] and [2+4] Type Cycloadditions of Isocyanates
with Ynolates
Mitsuru Shindo,* Akiko Harada, Kenji Matsumoto, and
Kozo Shishido
Azetidinedione
45
Pyridone
Ketene
Ynolate
Studies on the Preparation of 1,5-Methanoazocinoindole
Based on Indolylborate
Minoru Ishikura,* Norinobu Takahashi, Hidekazu Takahashi,
and Kazuo Yanada
Tandem Cyclization-Cross-Coupling Reaction
Indolylborate
Uleine
Catalytic Hydrogenation
Cyclization
HETEROCYCLES, Vol. 66, 2005
51
Practical Halogenations of Nucleosides Using
Tetrabutylammonium Peroxydisulfate
Vasu Sampath, Vidyadhar Jadhav, Hee Yoon Lee,*
and Yong Hae Kim*
Chlorination
57
Bromination
N-Bromosuccinimide
Regioselectivity
Pyrimidine
Direct Access to Heteropolycyclic Spiroketones.
1,3-Dichloroacetone as a Cyclopropanone Equivalent
Leo A. Paquette,* David G. Hilmey, and Peter R. Selvaraj
Oxonium Ion
61
Pinacolic Ring Expansion
Cyclopropanone Equivalent
Spirocyclic Ketone
Acid-catalyzed Rearrangement
A New Asymmetric Total Synthesis of Enantiopure
(-)-Malyngolide
Hidetoshi Miyamoto, Mitsuhiro Iwamoto, and
Masahisa Nakada*
Asymmetric Catalysis
69
Cyclopropanation
Enantioselective
Intramolecular Reaction
Stereoselective
Enantioselective Syntheses of Heliannuols G and H
Sachie Morimoto, Mitsuru Shindo, and Kozo Shishido*
Sesquiterpene
75
Lipase
Desymmetrization
Metathesis
Palladium-catalyzed Allylation
A Cation-Exchange Resin Promoted Imino Aldol Reaction
of Chiral Alkoxyketene Silyl Acetals with !,"-Unsaturated
Imines, Leading to a Facile Synthesis of "-Lactams
Makoto Shimizu,* Masanori Tachi, Shiho Fukushima, and
Iwao Hachiya
!-Lactam
Cation-Exchange Resin
!-Amino Ester
Chiral Ketene Silyl Acetal
",!-Unsaturated Imine
HETEROCYCLES, Vol. 66, 2005
81
Asymmetric Introduction of Nucleophiles to the 2-Position
of Pyrrolidine Ring through N-Acylpyrrolidinium Ion
Osamu Onomura, Takashi Ikeda, and Yoshihiro Matsumura*
Alkylation
87
Asymmetric Reaction
Iminium Ion
Pyrrolidine
A Highly Efficient Synthesis of Trispheridine through
a Construction of Tetrahydrophenanthridine Based on
a Microwave-assisted Thermal Electrocyclic Reaction
of an Aza 6#-Electron System
Teppei Kumemura, Tominari Choshi, Junko Yukawa,
Aya Hirose, Junko Nobuhiro, and Satoshi Hibino*
Microwave
91
Electrocyclic Reaction
Tetrahydrobenzo[c]isoquinoline
Trispheridine
Phenanthridine Alkaloid
The Synthesis of Heteroarylazulene
Taku Shoji, Shigeru Kikuchi, Shunji Ito, and Noboru Morita*
Azulene
95
Lithium Magnesate
Thiophene
Pyridine
Quinoline
Kinetic Resolution via the [2,3] Stevens Rearrangement
of Epimeric Six-membered Ammonium Ylides: A New
Entry to Enantio-enriched !-Amino Acid Derivatives
Eiji Tayama,* Hiroyuki Tanaka, and Takeshi Nakai
Stevens Rearrangement
101
Kinetic Resolution
Chirality Transfer
New Utilizations of Optically Active Homoallylamines:
Highly Stereoselective Synthesis of Cyclic Guanidine
and Thiourea
Reiko Yanada, Akira Kaieda, Kazuo Yanada, and
Yoshiji Takemoto*
Homoallylamine
Halocyclization
Imine
Indium
Guanidine
Ammonium Ylide
Unnatural Amino Acid
HETEROCYCLES, Vol. 66, 2005
107
A Concise Enantioselective Synthesis of
(+)-!-Conhydrine
Kazuhiro Nagata, Yosuke Toriizuka, and Takashi Itoh*
(+)-"-Conhydrine
111
Enantioselective Synthesis
Kinetic Resolution
Diastereoselective Reduction
2-(1-Hydroxypropyl)pyridine
Cu(II)-mediated Stereoselective Michael Addition of
a Methyl Group to an !,"-Unsaturated Ester as the
C2-Side Chain in 3-(t-Butyldimethylsilyloxy)tetrahydropyrans
Keisuke Suzuki, Ulrike Jannsen, Hiroko Matsukura, and
Tadashi Nakata*
Michael Addition
119
Methylation
",!-Unsaturated Ester
Methylmagnesium Bromide
Cyclic Ether
Anion-induced Fluorescence Quenching and Excimer
Formation of Anthracene-Imidazolium Receptor
Kiyoshi Sato,* Yuichi Sadamitsu, Sadao Arai,
Tetsuya Shimada, Haruo Inoue, and
Takamichi Yamagishi
C-H···X Hydrogen Bonding
129
Anion Recognition
Fluorescence Quenching
Imidazolium
Anthracene Excimer
Synthetic Studies of Liposidomycin Degradation Product:
Attempt for Introduction of an Uracil Group
Shouhei Fukunishi, Makoto Ubukata, and Noriyuki Nakajima*
Nucleoside Antibiotics
135
Peptidoglycan Synthesis Inhibitor
O-Nitrobenzenesulfonyl Group
Sterically Congested “Roofed” 2-Iminothioethers as
New Chiral Ligands for Palladium-catalyzed Asymmetric
Allylic Alkylation
Ryoh Tokuda, Hirofumi Matsunaga,* Tadao Ishizuka,
Makoto Nakajima, and Takehisa Kunieda*
2-Thiazolone
2-Thiazolidinone
2-Aminothiol
Electron Acceptor
Steric Factor
Synthesis
Caprazamycin
HETEROCYCLES, Vol. 66, 2005
143
Direct C-C Bond Formation between Thymine Derivatives
and Naphthalene through [2+2]-Photocycloaddition
Kazue Ohkura,* Tetsuya Ishihara, Hajime Takahashi,
Haruko Takechi, and Koh-ichi Seki*
Naphthocyclobutapyrimidine
147
Piperylene
Cyclobutane Ring Formation
Mode Selective Cycloaddition
Novel Protocol for the Asymmetric Synthesis of
3-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5benzothiazepin-4(5H)-one via Bakers’ Yeast Reduction
Takuzo Komiyama, Yutaka Takaguchi, and Sadao Tsuboi*
Deltiazem
153
Biocatalyst
1,5-Benzothiazepin-2-one
Darzens Condensation
Dichloroacetate
Sc(OTf)3-catalyzed C-Glycosylation of "-Diketones.
A Facile Access to Useful Precursors of Heteroaromatic
C-Glycosides
Takahito Yamauchi, Masayuki Shigeta, Takashi Matsumoto,*
and Keisuke Suzuki*
C-Nucleoside
161
C-Glycosylation
!-Diketone
Heteroaromatic
Scandium Tris(triflate)
Syntheses and Biological Activities of Structurally Stiff
Rhodacyanines as Novel Antimalarial Candidates
Kiyosei Takasu,* Daiki Morisaki, Marcel Kaiser, Reto Brun,
and Masataka Ihara*
Antimalarial Activity
167
Rhodacyanine Dye
Drug-Resistance
Structural Rigidification
Synthesis
An Enantio- and Diastereocontrolled Synthesis of
(+)-7-Deoxy-trans-dihydronarciclasine
Takashi Fujimura, Masatoshi Shibuya, Kunio Ogasawara,*
and Yoshiharu Iwabuchi*
Amaryllidaceae
Phenanthridone
Stereocontrolled Synthesis
Cyclohexanoid
Chiral Building Block
HETEROCYCLES, Vol. 66, 2005
175
1,3-Dipolar Cycloaddition of Ethyl 2,3-Pentadienoate
with Pyridinium Dicyanomethylides: Regiospecific
Formation of Ethyl 3-Cyano-2-ethylindolizine-1carboxylates and a Novel Formation of Tricyclic
Compounds
Naoto Hayashi, Naoto Kawajiri, Takane Uchida, and
Kiyoshi Matsumoto*
Pyridinium Ylide
181
1,3-Dipolar Cycloaddition
Allene
Indolizine
Regioselectivity
Diastereoselective Fischer-Type Pyrroloindole
Synthesis and Its Application to the Synthesis
of Chiral Pyrrolo-indole Alkaloids
Atsushi Nishida,* Satoru Ushigome, Ayako Sugimoto,
and Shigeru Arai
Asymmetric Synthesis
187
Esermethole
Fischer Indole Synthesis
Physostigmine
Pyrroloindole
Asymmetric Synthesis of Crypto-folione and
Determination of Its Absolute Configuration
Yuko Matsuoka, Kohsuke Aikawa, Ryo Irie, and
Tsutomu Katsuki*
Asymmetric Hetero-Diels-Alder Reaction
195
(Salen)chromium Complex
Cryptocarya Species
6-Substituted 5,6-Dihydro-"-pyrone
Regression Analysis in the Characterization of Hydrogenbonded Complex System Involving 2-Pyridone in Terms
of Melting Points before and after Complexation
Ichiro Takahashi,* Masahiro Takahashi, Hidehiko Kitajima,
Masami Wagi, Yumi Takahashi, Machiko Sabi,
Atsushi Hishida, Minoru Hatanaka, Kimio Isa, Akihito Yamano,
Akiyo Sakushima, and Shinzo Hosoi
Molecular Recognition
201
Hydrogen Bonding
Construction Module
Regression Analysis
Melting Poing
Bismuth Triflate-Chiral Bipyridine Complex Catalyzed
Asymmetric Ring Opening Reactions of meso-Epoxide
in Water
Chikako Ogawa, Stéphane Azoulay, and Sh# Kobayashi*
Bismuth Triflate
Chiral Bipyridine Ligand
Water
meso-Epoxide
Ring Opening Reaction
anti-1,3-Diol
HETEROCYCLES, Vol. 66, 2005
■ PAPERS
207
Synthesis and Transformations of Ethyl (2E)-3-N,NDimethylamino-2-(5-ethoxy-1-phenyl-1H-pyrazol-3-yl)propenoate
David Bevk, Ljubo Goli$, Amalija Golobi$, Jurij Svete, and
Branko Stanovnik*
1H-Pyrazole
3-Pyrazol-3-ylpropenoate
219
3-Heteroaryl-1H-pyrazole
Synthesis of (4R,5S)-Melithiazols B and M
Hiroyuki Akita,* Takamitsu Sasaki, Hiroyuki Takayama,
and Keisuke Kato
Melithiazol
229
!-Methoxyacrylate
Bithiazole
Natural Product Synthesis
Anitibiotics
Effective Methods for Introducing Some Aryl and
Heteroaryl Substituent onto 1-Azaazulene Nuclei
Noritaka Abe,* Megumi Tanaka, Takeshi Maeda,
Hiroyuki Fujii, and Akikazu Kakehi
1-Azaazulene
241
Aryllithium
Addition-Elimination
Suzuki Coupling
X-Ray Structure Analysis
Synthesis of Tetrahydro-"-carbolines via Radical
Cyclization of 2-Alkenylthioanilides
Manami Iwadate, Tohru Yamashita, Hidetoshi Tokuyama,
and Tohru Fukuyama*
!-Carboline
251
Indole
Thioamide
Radical Cyclization
Lawesson’s Reagent
Synthesis of Phospholane 1-Oxide Having Oxygen
Functional Groups from a 4-Bromobutylphoshinate
Derivative
Tadashi Hanaya,* Shigeru Kawase, and Hiroshi Yamamoto
Phospholane 1-Oxide
Phospha Sugar
Grignard Reaction
Michaelis-Arbuzov Reaction
SDMA
HETEROCYCLES, Vol. 66, 2005
263
Planar-Chiral Ionic Liquids. Cyclophane-Type Imidazolium
Salts with a C(2)-C(4) Bridge
Yasuhiro Ishida, Hiroyuki Miyauchi, and Kazuhiko Saigo*
Chiral Recognition
275
Cyclophane
Imidazolium
Ionic Liquid
Planar Chirality
Synthesis and Properties of (1-Azulenyl)di(3-indolyl)methylium Hexafluorophosphates
Shigeru Kikuchi,* Makiko Iki, Chizu Ikeda, and
Kimiaki Imafuku*
Indole
285
Azulene
(1-Azulenyl)di(3-indolyl)methyl Cation
pKR + Value
Stability
Allosteric Binding of Alkali Metal Ions to a Pseudocryptand Formed by a C-Pivot Tripodal Ligand
Containing 3-Hydroxy-2(1H)-pyridinone and Ga(III)
Akira Katoh,* Hidenori Kudo, and Ryota Saito
Allosteric Binding
299
Hexadentate Ligand
3-Hydroxy-2(1H)-pyridinone
Pseudocryptand
Alkali Metal Recognition
Synthesis of Novel 5-Acetoacetyl-3-acetyl-2-pyridone
Derivatives by the Ring-Transformation of 6-Methyl1,3-oxazin-4-ones
Hidekazu Ouchi,* Hisao Saito, Yutaka Yamamoto, and
Hiroki Takahata*
Ring Transformation
309
6-Methyl-1,3-oxazin-4-one
Isoxazole
5-Acetoacetyl-3-acetyl-2-pyridone
Poly-functionalized Pyridone
Hypervalent Iodine(III) Reagent-promoted Rearrangement
and Subsequent Oxidative Ring Cleavage of Cyclic 2,3Epoxy-1-alcohol Derivatives
Yasuyuki Kita,* Satoshi Matsuda, Eri Fujii, Shinji Kitagaki,
Ryoko Inoguchi, Kayoko Hata, and Hiromichi Fujioka
Tandem Reaction
"-Hydroxy Ketone Derivative
!-Hydroxy Ketone Derivative
%-Formylalkanoic Acid
Spirocyclic Lactone
HETEROCYCLES, Vol. 66, 2005
319
Novel 1,1’,5,5’-Tetraaryl-2,2’-bipyrroles: Their Synthesis
and Physical Properties
Shoji Matsumoto, Takamitsu Kobayashi, and Katsuyuki Ogura*
Pyrrole
333
2,2’-Bipyrrole
CuCl-catalyzed Cyclization Reaction
Flat Conformation
Twisted Conformation
Addition of 2-Oxazolidinones to Arylidenecyclopropanes:
A Highly Efficient Method for the Preparation of gem-Aryl
Disubstituted Homoallylic Oxazolidinones
Amal I. Siriwardana, Kalum K. A. D. S. Kathriarachchi,
Itaru Nakamura, and Yoshinori Yamamoto*
Hydroamination
341
Methylenecyclopropane
Oxazolidinone
Copper Catalyst
Homoallylation
Alternative Synthesis of (-)-Geissman-Waiss Lactone,
a Key Intermediate of Necine Bases
Toshio Honda* and Sae Matsumoto
Ring-closing Metathesis
347
Intramolecular Michael Reaction
Pyrrolizidine Alkaloid
Anti-malarial Piperidine Alkaloid
Guanidine-catalyzed Asymmetric Addition Reactions:
Michael Reaction of Cyclopentenone with Dibenzyl
Malonates and Epoxidation of Chalcone
Takuya Kumamoto, Keiko Ebine, Yukari Araki, Miyuki Endo,
Yuji Fushimi, Ikue Miyamoto, Tsutomu Ishikawa,*
Toshio Isobe, and Keiko Fukuda
Guanidine
361
Michael Reaction
Epoxidation
Enantioselective
Synthesis of Base-selectively Deuterium-labelled
Nucleosides by the Pd/C-catalyzed H-D Exchange
Reaction in Deuterium Oxide
Hiroyoshi Esaki, Fumiyo Aoki, Tomohiro Maegawa,
Kosaku Hirota, and Hironao Sajiki*
Deuterium
Nucleoside
Palladium
Deuterium Oxide
Green Chemistry
HETEROCYCLES, Vol. 66, 2005
371
Synthesis of a Pseudoenantiomer of "-Isocupreidine
("-ICD), a Chiral Amine Catalyst for Asymmetric
Baylis-Hillman Reactions
Ayako Nakano, Keisuke Takahashi, Jun Ishihara, and
Susumi Hatakeyama*
Organic Catalysis
385
Asymmetric Catalysis
Baylis-Hillman Reaction
!-Isocupreidine (!-ICD)
Quinine
Asymmetric Synthesis of "-Substituted $-Lactams
Employing the SAMP-/RAMP-Hydrazone Methodology.
Application to the Synthesis of (R)-(-)-Baclofen
Dieter Enders* and Oliver Niemeier
Lactam
405
Hydrazone
Nitrile
Alkylation
GABA Agonist
Remarkable Effect of Subtle Structural Change of
Chiral Pseudo-18-Crown-6 on Enantiomer-Selectivity
in Complexation with Chiral Amino Alcohols
Keiji Hirose,* Pakatip Aksharanandana, Michiko Suzuki,
Kiyoshi Wada, Koichiro Naemura, and Yoshito Tobe
Chiral Recognition
433
Crown Ether
Amine
Enthalpy and Entropy
Thermodynamics
Synthesis of New Chiral Bis-oxazoline Ligand with Zinc
Triflate-Selective Chelating Ability and Its Applications
Kazuishi Makino, Ikuko Ogawa, and Yasumasa Hamada*
Chiral Bis-oxazoline Ligand
441
Dihydroanthracene
Enantioselective Diels-Alder Reaction
Short-Step Synthesis of 5-Thio-L-hexopyranoses from
D-Glyconothio-O-lactones
Daisuke Sawada, Shinya Sasayama, Hideyo Takahashi,
and Shiro Ikegami*
L-Sugar
Thiosugar
Mitsunobu Cyclization
Thiosugar Lactone
Sugar Oxime
Henry Reaction
Zinc Triflate
HETEROCYCLES, Vol. 66, 2005
453
Synthesis of Di- and Trisaccharides Comprising
D-Fructopyranose with "2 % 1 Glycosidic Linkage
Using "-D-Fructopyranosyl Fluoride as the Fructosyl
Donor
Eisuke Kaji,* Emiko Kurimoto, Reiko Saiga, Ayako Matsuura,
Kazuho Harada, and Takashi Nishino
!-D-Fructopyranosyl Fluoride
469
Methoxymethyl !-D-Fructopyranoside
!(2 & 1)-Fructosylation
Fructooligosaccharide
Synthesis of 25-Hydroxy-19-norvitamin D3 Analogs and
Their Antiproliferative Activities on Prostate Cells
Midori A. Arai, Ryuji Tsutsumi, Hideki Hara, Tai C. Chen,
Toshiyuki Sakaki, Naoko Urushino, Kuniyo Inouye, and
Atsushi Kittaka*
19-Norvitamin D
481
Julia-Type Olefination
1"-Hydroxylase (CYP27B1)
Antiproliferative Activity
Efficient Synthesis of Functionalized Benzazepine
Derivatives Utilizing Intramolecular Mitsunobu Reaction
Tadaaki Ohtani,* Yoshikazu Kawano, Kazuyoshi Kitano,
Jun Matsubara, Makoto Komatsu, Minoru Uchida,
Fujio Tabusa, and Yoshimitsu Nagao
Cyclization
503
Mild Condition
Electron-withdrawing Group
Novel Synthesis of 4-Arylsulfenyl-3-hydroxy-2-pyrone:
One Pot Substitution-Rearrangement-Cyclization Reaction
of Acetonide Protected 4,5-Dihydroxy-2-chloroglycidic
Ester by Sodium Arylthiolate
Takuzo Komiyama, Yutaka Takaguchi, and Sadao Tsuboi*
One Pot Reaction
511
3-Hydroxy-2-pyrone
Cyclization
Darzens Condensation
Stereoselective Synthesis of 2,5-Di- and 2,2,5Trisubstituted Pyrrolidines by Allylation Reaction
of Acyliminium Ion
Tetsuro Shinada,* Makoto Hamada, Masanori Kawasaki,
and Yasufumi Ohfune*
Acyliminium Ion
Allylation
Pyrrolidine
Stereoselectivity
Dichloroacetate
Prostate Cell
HETEROCYCLES, Vol. 66, 2005
■ NOTES
527
Palladium-assisted Biaryl Coupling Reaction of
1-(2-Iodobenzoyl)-1,2,3,4-tetrahydroquinoline
Takashi Harayama,* Tomonori Sato, Akihiro Hori,
Hitoshi Abe, and Yasuo Takeuchi
Pyrido[3,2,1-de]phenanthridin-8-one
531
Biaryl Coupling
Pd Reagent
Benzoyltetrahydroquinoline
Benzoyldihydroindoline
Diol Derivative of (3-Trifluoromethyl)phenyldiazirine
for Post-labeling of Photocrosslink
Makoto Hashimoto* and Yasumaru Hatanaka
Diazirine
535
Photocrosslink
Diol
Avidin-Biotin
Schiff Base
Wittig Rearrangement of Ally 2-Thiophenemethyl Ethers:
Facile Synthesis of Thiophenemethanol and -ethanol
Derivatives
Masayoshi Tsubuki,* Sohichiro Matsuo, and Toshio Honda*
Wittig Rearrangement
543
2-Thiophenemethyl Ether
2-Thiophenemethanol
2-Thiopheneethanol
Direct C-C Coupling of meso-Octamethylcalix[4]pyrrole
with 6-Nitroazolopyrimidines
Oleg N. Chupakhin,* Nadezhda A. Itsikson,
Sergey Sh. Bashirov, Dmitry G. Beresnev,
and Gennady L. Rusinov
6-Nitroazolopyrimidine
549
meso-Octamethylcalix[4]pyrrole
Nucleophilic Addition
'H-Adduct
SNH--Process
Synthesis of (-)-5-Epiindolizidine 167B and Formal
Synthesis of 5E,9Z-Indolizidine 223AB
Naoki Toyooka* and Hideo Nemoto
(-)-5-Epiindolizidine 167B
5E,9Z-Indolizidine 223AB
Amphibian Skin
Enol Triflate
5-epi-1
167B
HETEROCYCLES, Vol. 66, 2005
557
Heterocycles from Ylides. Part IX. A Convenient Synthesis
of 1-Sulfonyl-2,3-disubstituted 2,3-Dihydroindoles
Giuseppe Cremonesi, Piero Dalla Croce,* and
Concetta La Rosa
2,3-Dihydroindole
563
Benzenesulfonamide
Sulfur Ylide
Cyclocondensation
Intermolecular Photoreaction of Benzenecarbothioamide
with $,&-Unsaturated Ketones: Application to Synthesis
of Cycloalkane [c]-Fused Pyridines
Kazuaki Oda,* Michiko Haneda, Naozumi Nishizono,* and
Minoru Machida
Paterno-Büchi Reaction
567
Thioamide
Highly Substituted Pyridine
Ring-fused Pyridine
Dirhodium(II) Tetrakis[N-benzene-fused Phthaloyl(S)-piperidinonate] as a Chiral Lewis Acid: Catalytic
Enantioselective Aldol Reactions of Acetate-derived
Silylketene Acetals and Aldehydes
Takuya Washio, Seiichi Nakamura, Masahiro Anada,
and Shunichi Hashimoto*
Aldol Reaction
579
Asymmetric Catalysis
Enantioselection
Dirhodium(II) Complex
Sily Ketne Acetal
Synthesis of 3-O-Alkylascorbic Acids from L-Ascorbic
Acid in a Single Step
Yasuo Kikugawa,* Takeshi Sakamoto, Shinya Sato, and
Kayoko Asami
Ascorbic Acid
583
3-O-Alkylascorbic Acid
Alkylation
Alkyl Mesylate
Solvent Effect on the Reaction of 1-Methoxy-3-(2nitrovinyl)indole with Nucleophiles
Koji Yamada, Tomoyuki Izumi, Fumio Yamada, and
Masanori Somei*
Solvent Effect
1-Methoxy-3-(2-nitrovinyl)indole
Michael Addition
Nucleophilic Substitution
Indole
HETEROCYCLES, Vol. 66, 2005
595
Reactions of 1,1-Bis(silylmethyl)-1-alkene with
N-Halosuccinimide and Ozone
Jun'ichi Uenishi,* Yusuke Tanaka, Masashi Ohmi,
Hotsumi Shimomura, and Nobuyuki Kawai
Allylsilane
603
Protodesilylation
Halodesilylation
Oxidative Desilylation
Ozone
Asymmetric Mannich-Type Addition of Lithium Glycolates
to Imines Producing 3-Hydroxy-4-phenylazetidin-2-ones
Hiroki Fujieda, Seiji Hata, Ken-ichi Yamada, and
Kiyoshi Tomioka*
Mannich Reaction
611
Lithium Enolate
Asymmetric Reaction
Chiral Ligand
!-Lactam
One-Step Synthesis of Ethyl Quinaldates by Lewis
Acid Catalyzed Three-Component Coupling Reaction
of Aromatic Amines, Aliphatic Aldehydes and Ethyl
Glyoxylate
Takashi Inada, Takayuki Nakajima, and Isao Shimizu*
Ytterbium Triflate
621
Quinaldic Acid
Three-Component Coupling Reaction
Palladium-catalyzed Cyclocotrimerization of Propargyl
Alcohols with Aryl Halides
Shuichi Oi,* Hideki Orihara, Hiroshi Kawai, and Yoshio Inoue*
Cyclization
627
Trimerization
Propargyl Alcohol
Aryl Halide
Palladium
Radical Reactions and !-Silylations of Optically Active
4-Trichloromethyl-"-lactone
T. Andrew Mitchell and Daniel Romo*
!-Lactone
Radical Alkylation
Dechlorination
"-Silylation
Amide
Quinoline Synthesis
HETEROCYCLES, Vol. 66, 2005
639
Spiro Crown Ethers Bearing (S)-1,1’-Spirobiindanes
as Chiral Backbones
Kohji Yonezawa, Mahesh L. Patil, Hiroaki Sasai, and
Shinobu Takizawa*
Spiro Skeleton
645
Crown Ether
Chiral Phase Transfer Catalyst
Enantioselective Alkylation
Asymmetric Synthesis
Hetero-Diels-Alder Reaction Catalyzedby Self-organized
Polymeric Rare Earth Complexes under Solvent-free
Conditions
Shuichi Ishida, Tetsuji Hayano, Hiroshi Furuno, and
Junji Inanaga*
Coordinated Polymer Complex
651
Self-oraganized Catalyst
Reusable Lweis Acid Catalyst
Scandium Sulfonate
Dihydropyranone
Two New Indole Alkaloids from Aspidosperma
subincanum and Geissospermum vellosii
Haruaki Ishiyama, Miyako Matsumoto, Mitsuhiro Sekiguchi,
Hideyuki Shigemori, Ayumi Ohsaki, and Jun'ichi Kobayashi*
Aspidosperma subincanum
659
Quaternary Indole Alkaloid
Subincanadine G
Geissospermum vellosii
Synthesis of N-Methylphenanthridinone Derivatives Fused
with a Silacyclohexane Ring by Radical Reaction Using
Tributyltin Hydride
Yuya Hoshino and Osamu Hoshino*
Phenanthridinone Derivative
667
2-Silatetralin
Radical Reaction
Cyclization
Tributyltin Hydride
The Structural Information of the Quaternary Ammonium
Salts Derived from Nicotine and Sparteine in the Solid
State
Kazuhiro Yoshizawa, Yasuko In, Toshimasa Ishida, and
Takayuki Shioiri*
Nicotine
Sparteine
Quaternary Ammonium Salt
X-Ray Crystallography
Benzylation
Pausperadine A
HETEROCYCLES, Vol. 66, 2005
675
Are Multicomponent Strecker Reactions of Diketones
with Diamines under High Pressure Amenable to
Heterocyclic Synthesis?
Koji Kumamoto, Hirokazu Iida, Hiroshi Hamana,
Hiyoshizo Kotsuki, and Kiyoshi Matsumoto*
High Pressure Reaction
683
Strecker Reaction
Multicomponent Reaction
Tetrahydrophenazine
Preparation of N-Sulfonyl-2-quinolinone Using
Ring-closing Metathesis (RCM)
Mitsuhiro Arisawa,* Chumpol Theeraladanon, and
Atsushi Nishida*
Ruthenium
Diels-Alder Reaction
2-Quinolinone
Metathesis
■ REVIEWS
689
Anion Receptors
Oleg N. Chupakhin,* Nadezhda A. Itsikson,
Yuri Yu. Morzherin, and Valery N. Charushin
Anion Receptor
711
Supramolecular Chemistry
Macrocycle
Calixpyrrole
Urea
Enantiotopic Synthesis of Natural Products: Merrilactone
and Guanacastepene
Heedong Yun, Zhaoyang Meng, and Samuel J. Danishefsky*
Total Synthesis
Enantioselective
Merrilactone A
Guanacastepene A
Natural Product
Tetrahydrodibenzo[b,f][1,4]diazocine
HETEROCYCLES, Vol. 66, 2005
727
Synthetic Strategies of Fostriecin
Masakatsu Shibasaki* and Motomu Kanai
Fostriecin
743
Serine/Threonine Protein Phosphatase Inhibitor
Asymmetric Catalyst
Structure-Activity Relationship
Expanding Structural Diversity of Terpene Trilactones
from Ginkgo biloba Extract: Studies towards Coremodified Ginkgolides
Sergei V. Dzyuba,* Sergei Bolshakov, Jean Li, and
Koji Nakanishi*
Ginkgolide
Ring-opening
■ INDEXES
753
769
Author Index
Subject Index
Skeleton Rearrangement
Lactone Reduction
Metathesis