htr_main (jielde)

HETEROCYCLES, Vol. 54, No. 2, 2001
■ COMMUNICATIONS
561
Synthesis and Biological Evaluation of Water Soluble
Taxoids Bearing Sugar Moieties
glycosyl O ( )
n
Yoshinori Tsuchiya, Kosho Nakamura, Tetsuya Amano,
Wakao Iwatani, Ko-zo Hara, Ko-ji Hara, Katsuhiko Mikuni,
Katsuyoshi Nakanishi, Tetsuta Oshitari, Hiroshi Okumoto,
and Tadakatsu Mandai*
O
O
O
O
O
NH
Ph
OH
O
O
OH
HO OBz OAc
O
n = 0, 2�4, 6, 8
glycosyl = glucosyl, galactosyl, mannosyl
Paclitaxel
567
Docetaxel
Acylating Agent
Water Soluble Taxoid
Anticancer Agent
Photochemistry of Heterocyclic Cage Compound:
Photoreaction of 2,7-Dihydroazepine to Give 2,3Dihydroazepine and Photoreaction of the 2,3Dihydroazepine to Form 1,2-Dihydroaniline
N
Yoshitaka Emoto and Katsuhiro Saito*
O
571
Time Dependence
Solvent Effect
Triplet Sensitization
h!
O
Cl4
O
Diradical
Ionic Character
CO2H
O
Cl4
Ar1
O
O
H+
OR
H
120.0
4.6
H
Takenori Kusumi, Kyoko Utsumi, and Takashi Ooi*
124.0
3.9
116.5
9.6
Br
Br
136.7
16.7
H ! 7.34
Brittle Star
Indole
13
92.9
7.9
115.5
7.6
125.7
15.6
Br
112.5
4.5
N
CH3
32.4
7.7
13C chemical shift (!/ppm)
T1 values (sec)
C NMR Spectrometry
Efficient Stereoselective Synthesis of (2S,3S,5R)(+)-Preussin
Henryk Gruza, Antoni Krasinski, and Janusz Jurczak*
HO
Ph
Allylic Addition
!-Amino Aldehyde
Diastereoselectivity
Antifungal Agent
N
Me
C9H19
Ar1
Ar2
Electron-withdrawing Group
Carbon-13 Spin-Lattice Relaxation Time (T1) for
Assignment of Brominated Carbons
Marine Natural Product
NHCO2Et
Ring Contraction
Ar2
581
N
Acid-catalyzed Cycloaromatization of Enediyne
Model Compounds via Enyne-Allene Intermediates
Hisao Nemoto, Akira Shigenaga, Ichiro Suzuki, and
Masayuki Shibuya*
577
CO2Et
O
O
Cl4
Photorearrangement
CO2Et
Ph
HNCbz
H
O
Me3Si
HETEROCYCLES, Vol. 54, No. 2, 2001
585
Diastereocontrol in the Reaction of (R)-2,2-Dimethyl-4acyl-1,3-dioxolanes with Alkylmetals: A Facile Entry to
Enantiopure Terpenetriols
Koichi Mikami, Hisashi Mikoshiba, and Takeshi Nakai*
O
H
n
O
O
Me OH
H
MeLi , SnO4
n
>95% anti
n = 1, 2
Gymnoprenol
589
Asymmetric Synthesis
Glycerketone Acetonide
Organometallic Addition
Synthesis of !-(Trifluoromethyl)pyrrolidines by
Cyclization of N-Tosyl-!-(trifluoromethyl)homoallylamine
Derivatives
Trifluoromethyl
593
Fluorine
Pyrrolidine
Cyclization
Facile Conversion of Trialkylsilyl Esters to Alkyl Esters
Mediated by Tetrabutylammonium Fluoride Trihydrate
Deprotection
Alkyl Halide
Lactone
R
CF3
R
N
Ts
TBAF 3H2O (1.1 eq)
R2X (1.1�2.0 eq)
O
R1
Alkylation
X
X+
Ene Reaction
Hayato Sugimoto, Takashi Ooi, and Keiji Maruoka*
597
Chelation Model
CF3
TsNH C
H
Akira Ando, Masaaki Omote, Kazuyuki Sato,
Shuichi Jonoshita, and Itsumaro Kumadaki*
O
O
OSiMe3
O
R1
THF
rt, 1.5 h
OR2
85�96%
Ammonium Carboxylate
A Molecule Detection Sensor of Modified Cyclodextrin
Based on Guest-responsive Intramolecular Fluorescence
Quenching
Taiyo Aoyagi, Toshinao Yamasaki, Akio Yoshida, and
Akihiko Ueno*
Modified Cyclodextrin
601
Pyrene
Host-Guest Complex
Nitrobenzene
Studies on Pyrimidine-annulated Heterocycles:
Synthesis and Function of Novel 9-Substituted
Cyclohepta[b]pyrimido[5,4-d]furan-8,10(9H)-diones
Yutaka Mizuta, Tohru Takayasu, and Makoto Nitta*
O
Fluorescence Quenching
H
N
O
O
Cl
NR1
R1 = Me, Bu, Ph
O
R2
O
N
O
R3
CH OH
R2
R3
C
O
Cyclohepta[b]pyrimido[5,4-d]furan-8,10(9H)-dione
Heteroazulene
2-Chlorotropone
O
NR1
NR1
O
H
N
O
H2O2
Barbituric Acid
O2
H
O
HETEROCYCLES, Vol. 54, No. 2, 2001
607
Synthesis of a Novel Artemisinin Analogue Having
Potent Antimalarial Activity
H
Yusuke Wataya, Hye-Sook Kim, Masahiro Toyota,
Yuko Tanaka, Ruriko Katagiri, Kiyosei Takasu, and
Masataka Ihara*
O
O
O
O
H
OH
CO2Me
H
Antimalarial Activity
611
1,2,4-Trioxane
Artemisinin
Octalone
R
1,3-Dipolar Cycloaddition of 1-Phenylpropa-1,2-diene with
Pyridinium Dicyanomethylides: 1-Phenylpropa-1,2-diene
as a Synthetic Equivalent of 1-Phenylpropyne
Ph
N+
Akikazu Kakehi, Kinuyo Aoyama, Naoto Hayashi, Yukio Ikemi,
Takane Uchida, Naoki Tanaka, and Kiyoshi Matsumoto*
- CN
C
CN
1 (R = H, Me, CN)
+
H
H
C
C
C
+
615
Pyridinium Ylide
Allene
Indolizine A
CN
X-Ray Analysis
Chiral Ketone-catalyzed Asymmetric Epoxidation of
Stilbene with Oxone®
Ph
Koichiro Matsumoto and Kiyoshi Tomioka*
619
Epoxidation
Dioxirane
Ph
RO2S N
Ph
Asymmetric Reaction
Olefin
N SO2R
N
Cl
N
Cl
HO
+
NaH
H2N
90%
O2, salcomine
83%
623
Ph
Quinonimine Structure
Cyclization
N
O
N
N
N
O
N
N
H
Makoto Nakajima, Hisae Okubo, Yoshimasa Yanamoto,
Shinji Kitagaki, and Shunichi Hashimoto*
Salcomine Oxidation
O
R3
R1
R2
SPh
N2
CO2R
Rh2(S-PTPI)4
R3
R1
R2
*
*
CO2R
SPh
up to 58% ee
Diazoacetate
Ph
O
Enantiocontrol in Tandem Allylic Sulfonium Ylide
Generation and [2,3] Sigmatropic Rearrangement
Catalyzed by Chiral Dirhodium(II) Complexes
Rhodium(II) Carbene Intermediate
O
Ketone
Takao Yamori, Sadamu Yoshida, Fusae Miyata, and
Tadashi Katoh*
Naphthoxazine Derivative
Oxone®, base
O
Ph
An Efficient and Expeditious Synthesis of a Novel
5H-Naphth[1',2':5,6][1,4]oxazino[2,3-b]quinoxalin-5one and Its Unique Inhibitory Activity against a Panel
of Human Cancer Cell Lines
Quinoxaline Derivative
CN
Ph
N
5
1,3-Dipolar Cycloaddition
4
Me
R
Me
N
toluene
H
2
Ph
R
!
Allylic Sulfide
N
H
N
O
Rh
Rh
O
Rh2(S-PTPI)4
HETEROCYCLES, Vol. 54, No. 2, 2001
629
Intramolecular Oxymercuration of 4-Hexen-1-ols:
Kinetic vs. Thermodynamic Products Regulated
by Mercuric Salts
O
Hg(OAc)2
Takumichi Sugihara, Hiroshi Imagawa, Hiroko Takao,
Kazuya Takahashi, Akihito Wakabayashi,
Masahiro Sakakibara, Terumi Kashima, and
Mugio Nishizawa*
then aq. NaCl
Me
OH
O
Hg(OTf)2, TMU
H HgCl
H
Me
H
then aq. NaCl
Oxymercuration
635
Mercuric Triflate
Mercuric Acetate
5-exo-Cyclization
Me
HgCl
6-endo-Cyclization
CHO
Application of Phthalimidine Synthesis with Use of
1,2,3-1H-Benzotriazole and 2-Mercaptoethanol as
Dual Synthetic Auxiliaries. 2. Effective Synthesis of
Phthalimidines Possessing Bulky Group at 2-Position
R1
+
N C R2
Motohiro Tanaka, Akihiko Nomura, Hiroyuki Uchida,
Minoru Hatanaka, Hidehiko Kitajima, Takanori Tamura,
Shigeki Kamimura, Etsushi Hirano, Mako Kimino,
Teruki Kawakami, and Ichiro Takahashi*
R1
R3
O
CHO
H2N C R2
R3
Double Mannich Reaction
639
Protonic Acid
Mild Condition
Isoindole Derivative
Structure of Sanggenon O, a Diels-Alder Type Adduct
Derived from a Chalcone and a Dehydroprenylated
Sanggenon-Type Flavanone from Morus cathayana
Bioactivity
HO
OH
Toshio Fukai, Ya-Qin Shi, and Taro Nomura*
O
H
H
HO
H
HO
Revised Structure
Sanggenon O
Absolute Structure
Moraceae
O
OH
O
O
OH
OH
OH
Mulberry Tree
■ PAPERS
647
New Synthetic Approach to Azuleno[1,2-c]pyrroles
and Conversion to Benz[a]azulenes
NH2
R1
Dao-Lin Wang and Kimiaki Imafuku*
R1
CH2Br
COMe
3 a, b
R2
6 a-d
N
Me
7 ab-ad, ba-bd
1-Acetylazulene
Aniline
Cyclization
Cycloaddition
Azuleno[1,2-c]pyrrole
R2
HETEROCYCLES, Vol. 54, No. 2, 2001
667
Reaction of 2-Aminoazulenes with Aldehydes. One
Pot Synthesis of Diazuleno[2,1-b:1,2-e]pyridines
N
Toyonobu Asao, Shunji Ito, Tomomi Terazono,
Tetsuo Okujima, and Noboru Morita*
RCHO
NH2
AcOH
R
R = H, Ph
Azulene
679
Acid-catalyzed Condensation
Pyridine Derivative
Basicity
Di(1-azulenyl)methane
An Efficient Preparation of 2H-Cyclohepta[b]furan2-ones
H
Shunji Ito, Ryuji Yokoyama, Masao Kudo, and
Noboru Morita*
H
c
H
O
H
O
Cl
Cl
O
Cl
Cl
H
H
a: MeCO3H
Cycloaddition
691
Dichloroketene
Oxidation
O
H
c
O
c
H
a
O
O
Cl
O
Dehydrochlorination
R2
R2
S
H
Ph
R1
Ph
N
CO2Me
R2
R2
Thiocarbonyl Compound
1,3-Dipolar Cycloaddition
N
H
R1
CO2Me
R2
R2
S
Ph
S
H
705
O
c: m-CPBA
b: LiCl or Li2CO3
Anthony Linden, Andreas Gebert, and Heinz Heimgartner*
Azomethine Ylide
O
Cl
Cl
Synthesis of 1,3-Thiazolidines from Aromatic Thioketones
and N-Benzylidene !-Amino Acid Esters via 1,3-Dipolar
Cycloaddition of Azomethine Ylides
!-Amino Acid Imine
O
Cl
b
O
Cl
Cl
O
b
O
X-Ray Crystallography
R1
N
H
CO2Me
Ar
Preparation of Meso-unsubstituted Porphyrins
Substituted with Mono- and Tetraformyl and Other
Electron-withdrawing Groups
X
Takashi Murashima, Hidemitsu Uno, Yumiko Fumoto, and
Noboru Ono*
Ar
N
H
Me
CO2Et
Ar
N
H
Y
Me
Ar
NH
CO2Et
N
N
HN
Ar
X = CO2Et, CN
Me
Me
Ar
Y = CO2Et, CH2OH
CHO, CN
4-Ethoxycarbonylpyrrole
721
4-Cyanopyrrole
"-Monoethoxycarbonylporphyrin
The Identification, Mechanism, and Improved Synthesis
of a New and Unique Heterocyclic System with a Fused
Imidazole Ring
"-Monoformylporphyrin
N
RCH2NH2
Jianwei Ren, Ashraf A. Khalil, Isamu Katsuyama, and
Jordan K. Zjawiony*
O
Sampangine Derivative
Arylalkylamine
Condensation
Cyclization
"-Monocyanoporphyrin
N
R = PhCH2, Ph
N
N
N
R
HETEROCYCLES, Vol. 54, No. 2, 2001
727
Synthesis of Brevicompanines, Plant Growth Regulators
O
Koji Matsumura and Takeshi Kitahara*
NH
N
R
N H
O
H
brevicompanine A
brevicompanine B
R=
D-Amino Acid
735
Diketopiperazine Ring
R=
Cyclization
Stereospecific Substitution of 1-(2-Pyridinyl)ethyl
Methanesulfonate with S- and O-Nucleophiles
Osamu Yonemitsu, Tomoko Takagi, Masahiro Hamada,
and Jun'ichi Uenishi*
N
S- or O-nucleophiles
Me
DMSO: THF (1: 0�1)
OMs
Me
N
Nu
Nu= SAr, S-alkyl, SAc
OAr, OAc, OBz
Chiral Pyridine
747
Substitution Reaction
Pyridine Ligand
Pyridinylethyl Alcohol
Pyridinylethyl Mercaptane
SiMe3
Regioselective Synthesis of Bridged Azabicyclic
Compounds Using Radical Translocation/Cyclization
Reactions of 4-Alkynyl-1-(o-iodobenzoyl)piperidines
( )n
Jun'ichi Uenishi, Yuko Nakano, Kazuya Okamoto,
Tatsunori Sato, and Masazumi Ikeda*
I
N
AIBN
n = 1, 2
O
2-Azabicyclo[3.2.1]octane
757
Morphan
SiMe3
Bu3SnH
1,5-Hydrogen Transfer
!-Acylamino Radical
N
Tributyltin Hydride
Synthesis and Properties of Benzimidazole and
Naphthoimidazole Derivatives of Perylenedicarboximide
Tokiko Uchida, Kozo Kozawa, Koji Tsuda, and
Yukinori Nagao*
PhCO
( )n
H2N
O
O
R N
O
O
O
H2N
O
O
R N
N
O
N
R = Me, Et, n-Pr, n-Bu, n-C5H11, n-C6H13, n-C8H17
n-C10H21, n-C12H25, n-C14H29, n-C16H33, n-C18H37
Perylenedicarboximide
765
Imidazole
Absorption Spectrum
Thermal Stability
Solubility
Intramolecular Photocycloaddition of 2-Cycloalkenyl-1,3dioxin-4-one. Stereoselective Synthesis of cis-Eudesmane
-4,11-diols
Hitoshi Takeshita, Akira Mori, Ka Li, and Toshihide Hatsui*
O
O
O
1,3-Dioxin-4-one
cis-Decalin
Eudesmane-4,11-diol
Photo [2+2] Cycloaddition
O
h!
O
O
!,"-Unsaturated Ester
HO
H
OH
HETEROCYCLES, Vol. 54, No. 2, 2001
777
h!
Photoinduced Electron-Transfer Reactions between C60
and Cyclic Disiliranes (c-R2Si-X-SiR2; X=SiR2, CH2, O,
NPh, S)
e-
R2Si
Yasuhiro Nakadaira, Masahiro Kako, Shigeru Nagase,
Kaoru Kobayashi, Takeshi Akasaka, Takatsugu Wakahara,
Yutaka Maeda, Mamoru Fujitsuka, Yoshiko Sasaki, and
Osamu Ito*
X
R2Si
X = SiR3, CH2, O, NPh, S
Photo-Adduct
789
Fullerene Photochemistry
Laser Photolysis
Photoinduced Electron Transfer
Synthesis of Ciguatoxin (2S,5R)-ABC Segment
Rungnapha Saeeng and Minoru Isobe*
Co2(CO)6 H
OPiv
PivO
C60 Triplet State
HO
OMe
BF3 OEt2
PivO
CH2Cl2
C-Glycosidation
Acetylene Biscobalthexacarbonyl
799
Acid Cyclization
OH SEt
H
OH
Co2(CO)6 H
H
O
OH
O
H H OHH
OPiv
Reductive Decomplexation
Cyclophane
Diels-Alder Reaction
SN2(Ar) Reaction
Tos N Cl
!
Cl
N
Cl
1,2,3,4-Tetrahydropyrrolo[3,2,1-hi]indole
-e
Substitution vs Addition. Regioselective Electrobromination of Benzofuran
NH4Br-AcOH, H2O (100/1)
or NaBr-CH2Cl2, H2O (1/1)
O
Sigeru Torii, Manabu Kuroboshi, Yusuke Kawakami,
and Hideo Tanaka*
Br
or
O
Electrolysis
833
SEt
3-Aza[5]metacyclophanes: Synthesis and Reactions
Anthony L. Spek, Willem H. de Wolf,
Franciscus J. J. de Kanter, Marianne de Rijke, Arne Egberts,
Norbert Gret, Stephen N'Krumah, Maurice J. van Eis,
Daniël S. van Es, and Friedrich Bickelhaupt*
825
H
H
O
Bromination
5-Bromobenzofuran
Syntheses, Structure and Conducting Properties
of Halogenated Ethylenedioxytetrathiafulvalenes
Toshiaki Enoki, Akira Miyazaki, Jun-ichi Nishijo,
Naoki Yoneyama, Takehiro Kato, Isao Ikemoto,
Hiroyuki Nishikawa, Haruo Matsuyama, Masato Yoshida,
Kohei Ugawa, Jun-ichi Takano, Koji Takeda, Takahiro Takano,
Hironori Suzuki, Kenji Hara, Eiji Ogura, Yoshiyuki Kuwatani,
and Masahiko Iyoda*
O
Tetrathiafulvalene
Donor
Electrical Conductor
Benzofuran
O
S
S
1) base (2 equiv.)
O
S
S
2) halogenation
O
S
O
S
O
S + O
S
X
S
X
S
P(OR)3
O
S
S
X
O
S
S
X
O
S
S
X
O
S
S
X
S
S
I
O
S
Br
O
S
Cl
S
S
I
S
S
O
EDO-TTFBr2
Br
S
S
O
EDO-TTFCl2
Cl
EDO-TTFI2
Halogenated Compound
Br
O
X = H, Br
X
2,3-Dibromo-2,3-dihydrobenzofuran
Br
X-Ray Crystal Structure
S
HETEROCYCLES, Vol. 54, No. 2, 2001
849
Intramolecular Complex Formation between Flexible
Molecular Tweezers and Weak Electron Acceptor
O
O
O
O
Hirotaka Kurebayashi and Yoshimasa Fukazawa*
N
O
O
Intramolecular Charge Transfer Interaction
865
Molecular Mechanics
X-Ray Crystallography
Short-Step Synthesis of Some Santanolides, Dehydroisoerivanin, Isoerivanin, Ludovicin C, and 1!,3!Dihydroxyarbusculin B by the Use of the Organoselenium
Reduction Method of Epoxy Ketones
Toshio Suzuki and Masaaki Miyashita*
O
O
Chemical Shift Simulation
HO
O
Na[PhSeB(OEt)3]
AcOH, EtOH
O
O
80%
O
O
O
O
O
dehydroisoerivanin
"-Hydroxy Ketone
871
1,3-Diol
Sesquiterpene Lactone
#-Lactone
Synthetic Studies on Halichlorine and Pinnaic Acid:
Palladium-mediated Construction of the Bicyclic
Spiro Core
Reductive Cleavage
O
VCAM-1
887
Alkaloid
Piperidine
Baker's Yeast
H
H
Cl
Mitsuru Shindo, Wakako Yokota, and Kozo Shishido*
H
N
O
Pd (0)
O
H
N
O
+
O
H
N
O
Spiro Ring
Synthesis of Indeno[1,2-b]phenanthrene-Type
Heterocycles by Cycloaromatization of Acyclic
Non-conjugated Benzotetraynes
TMS
HO
TMS
Fukuko Ueno, Kazuhiro Miyawaki, and Ikuo Ueda*
OH
R Q
3 : Q = O, S,
Thermolysis
901
Intramolecular Annulation
Stille Reaction
Q
NR1
V. Kren, N. Skottová, R. Gazák, P. Halada, P. Sedmera,
J. Kubisch, and Vilím Simánek*
4 : Q = O, S, NR1
1,4-Bistrimethylbuta-1,3-diyne
Chemoenzymatic Preparation of Oligoglycosides of
Silybin, the Flavonolignan from Silybum marianum
16
HO
8
8a
A
5
OH
4a
1
B
C
13
O
4
23
16a
O
9
*
12a
O
*
12
OH
O
1 R=H
2 R = !-D-glucopyranosyl
3 R = !-D-galactopyranosyl
Antioxidant
Low Density Lipoprotein
Flavonolignan
H
Enzymatic Glycosylation
Radical Scavenger
CH2OR
17
19
OMe
OH
HETEROCYCLES, Vol. 54, No. 2, 2001
917
CF3
N
N
Synthesis of Alternariolide Analogs for PhotoaffinityLabeling
Kimiko Hashimoto, Toshikatsu Okuno, Chikanori Morita,
and Haruhisa Shirahama*
X
HN
CONH
COO
CONH
NO2
CO
X = CH2, O
Host-specific Phytotoxin
929
3-(3-Nitro-4-alkyl)- and 3-(3-Nitro-4-alkoxy)phenyl-3-trifluoromethyldiazirines
AM-Toxin
Peptide
NMe2
Synthesis, Structure and Spectroscopic Characteristics
of 2'-Boryl-4''-dimethylaminochalcones. Effect of an
Intramolecular Boron-Oxygen Coordinate Bond to the
Conjugated System
Shigenobu Yano, Masako Kato, Yuji Mikata,
Yoshikazu Sugihara, Tomokazu Moriya,
Sachiko Yanagimoto, Kenji Sugimoto, and
Toshihiro Murafuji*
O
BR2
Organoboron
943
Chromophore
Solvatochromism
Equilibrium
Dipole Moment
Preparation of Benzoheterocycles Containing Group
14 Elements Using Zirconacyclopentadienes
Feng Xu, Fu-Yu Tsai, Yasuyuki Ura, Yanzhong Li, and
Tamotsu Takahashi*
R1
R2
Y
R3
R5
R3
1) Cp2ZrBu2
R4
5
R6
2) R
CuCl or NiX2(PPh3)2
Y
R6
R4
Y = Si, Ge, Sn
Benzosilacycle
957
Benzogermacycle
Benzostannacycle
Zirconacycle
Zirconocene
O
Chemical Constituents of Two Oriental Orchids,
Calanthe discolor and C. liukiuensis: Precursor
Indole Glycoside of Tryptanthrin and Indirubin
HO
Hisashi Matsuda, Tetsuo Sakurama, Akinobu Kishi,
Toshiyuki Murakami, and Masayuki Yoshikawa*
OO
OH
HO
HO
H
OH
967
Indole S,O-Bisdesmoside
Calanthoside
Synthesis of 2,3,4,5-Tetrahydro-1H-2-benzazepines
via Pummerer-Type Cyclization of N-Arylmethyl-N(3-phenylsulfinylpropyl)formamides
O
tryptanthrin (6)
N
H
S
Glucoindican
R3
Thionium Ion
H
N
O
O
R1
R4
O
Trifluoroacetic Anhydride
N
H
isatin (10)
Calaphenanthreol
S
Ph
Pummerer
reaction
N
R2
R3
CHO
R2
R3
Pummerer Reaction
O
O
indirubin (7)
NiCl2-NaBH4
1H-2-Benzazepine
H
N
H+
H
OH
R2
Jun Toda, Tomoko Kimura, Konomi Honda, Sachiko Terakado,
Toshiaki Saitoh, Yoshie Horiguchi, and Takehiro Sano*
N
O calanthoside (1)
OH
HO
Chinese Traditional Medicine
N
!-glucosidase
BF3·Et2O
R1
Ph
N
R4
R1
R4
S
CHO
R1, R2, R3, R4 = OMe
N
CHO
R1
R2
HETEROCYCLES, Vol. 54, No. 2, 2001
■ NOTE
985
Palladium-catalyzed Carbonylative Coupling of
Hypervalent Iodonium Salts with Amidoximes:
Synthesis of Oxadiazoles
Young-Taek Hong, Hyung-Chul Ryu, and Suk-Ku Kang*
Palladium-catalyzed Reaction
989
ArI+Ph X-
Carbonylative Cross-Coupling Reaction
NOH
R
R
PdCl2 (10 mol %)
NH2
N
K2CO3 (2 equiv)
NMP, toluene, 95 °C
7 h, CO (1 atm)
Hypervalent Iodine Compound
Oxadiazole
N
Ar
O
Cyclodehydration
HO
Synthesis and Pharmacological Evaluation of 18,19Dehydrobuprenorphine
Lucia Negri, Roberta Lattanzi, Klaus Wurst, Roland Krassnig,
Johannes Schütz, and Helmut Schmidhammer*
O
N
MeO
HO
Morphinan
999
Buprenorphine Analogue
Dehydrobuprenorphine
Analgesic
Two Taxoids from Taxus cuspidata as Modulators
of Multidrag Resistant Tumor Cells
Opioid
OH
AcO
Takashi Tsuruo, Akihiro Tomida, Katutoshi Hirose,
Naonori Hirata, Shujun Zhang, Katsuhiko Kosugi,
Hirofumi Sasaki, Jun-ichi Sakai, and Masayoshi Ando*
O
AcO
O
OR
H
H OAc
O
1
O
R = cinnamoyl :
Taxane Diterpene
1011
Taxus cuspidata
O
O
CH
R1CONHNH
Slovenko Polanc, Franc Pozgan, and Marijan Ko$evar*
N
Cl
1021
Pyrazol-3- and 5-one
Pyridazine
N
Ph
N
Cl
R3
Amide
N
2
2'
3'
Ph
N
N
R1
R2NH2
R2NHCOR1
O
N
NHNHCOR1
R3
R4
N
NH
PhCONH
R1 = Me, Ar; R2 = CHMePh, Ar; R3 = H, Me
R4 = H, 6-chloropyridazin-3-yl
Zirconium(IV) Chloride
X
5-endo-trig Radical Cyclization of N-Benzyl-2-haloN-(6-oxo-1-cyclohexen-1-yl)acetamides
Tatsunori Sato, Shinji Ohtani, Serry A. A. El Bialy, and
Masazumi Ikeda*
O
N
Bn
O
Bu3SnH
AlBN
H
X = Cl, I
O
Octahydro-7a-hydroxyindole-2,7-dione
1'
OR
H
H OAc
Modulator of Multidrug Resistant Tumor Cell
4-Acylhydrazinomethylene-2-phenyloxazol-5(4H)-ones
as Acylating Agents: Synthesis of Salicylanilides and
1,2,4-Triazolo[4,3-b]pyridazines
Hydrazide
OAc
N-Vinylic !-Haloacetamide
Capto-dative Effect
H
H
N
Bn
Tributyltin Hydride
O
+
O
N
OH
Bn
5-Membered Lactam
O
HETEROCYCLES, Vol. 54, No. 2, 2001
1027
Photosubstitution Reaction of Cyanoaromatics with
Aliphatic Amides
R1
Hajime Kubo, Takayasu Yamauchi, Kimio Higashiyama,
Moriya Tsuji, and Shigeru Ohmiya*
CHO
O
Single Electron Transfer
1033
2-Pyrrolidone
O
N
NC
R3
R3
R
MeO2C
-O
Titanium Tetrachloride
CHO
or
CN
Formation of Trisubstituted "-Butyrolactones by
Novel Ring Transformation of 2-Isoxazoline-2-oxides
2-Tetrahydrofuranone
R2
N
NC
h!
N
!-Arylamide
Seiko Hirotani, Keita Kumazawa, Kuniaki Sasaki,
Kazuho Harada, and Eisuke Kaji*
1039
CN
N
or
R1
R2
TiCl4
N+
CO2Me
1
a: R = Cl
b: R = Br
3H-Indole 1-Oxide
Single Crystal X-Ray Analysis
reflux
overnight
O
R
OH
N
O
H
2 3
1
4
O
H
Cl
CO2Me
2
Chlorination of Aromatic Ring
O
Haterumaimides A-E, Five New DichlorolissoclimideType Diterpenoids from an Ascidian, Lissoclinum Sp.
Katsuhiro Ueda, Kiyotake Suenaga, Susumu Kokubo,
Md. Jasim Uddin, and Daisuke Uemura*
NH
O
OH
Cl
Cl
H
OAc
haterumaimide A
Cytotoxicity
1049
Dichlorolissoclimide-Type
Diterpenoid
Stereochemistry
Synthesis of a Macroheterocyclic Compound through
Photodecarboxylation of Potassium #-Phthalimidoalkynoate
Michael Oelgemöller, Eun Young Kim, Dong Jin Yoo,
and Sang Chul Shim*
HO2C
O
( )n
N
%-Phthalimidoalkynoate
Internal Acetylene
OH
N
O
O
Photodecarboxylative Cyclization
( )n
Macroheterocyclic Compound
HETEROCYCLES, Vol. 54, No. 2, 2001
■ REVIEWS
1057
1095
Sesquiterpene Lactones and Acetogenin Lactones
from the Hepaticae and Chemosystematics of the
Liverworts Frullania, Plagiochila and Porella
Lahlou El Hassane, Toshihiro Hashimoto, Fumihiro
Nagashima, Masao Toyota, and Yoshinori Asakawa*
O
Bryophyte
Pinguisane
Sesquiterpenoid
Biological Activity
2,3-Secoaromadendrane
Cycloadditions of !,$-Unsaturated N,N-Dimethylhydrazones. A Diels-Alder Strategy for the Building
of Aza-Hetero Rings
1139
Dienophile
H
R2
R1
Hetero Diels-Alder Reaction
O
H
OH
CHO
R3
Zouhair Bouaziz, Pascal Nebois, Félix Pautet, and
Houda Fillion*
1-Azadiene
O
Quinone
[4+2]
cycloadducts
N
NMe2
Regioselectivity
Quinoline Alkaloids of Orixa japonica
OMe
Toshiro Noshita, Kiyoshi Murata, and Shinji Funayama*
O
O
N
OMe
O
MeO
O
N
Me
R = H, OMe
Biosynthesis
■ INDEXES
1149
1169
Author Index
Subject Index
Absolute Stereochemistry
Biological Activity
Johzan
R
Ph