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Graphical Abstract Angew. Chem. Int. Ed. 432003

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Contents
The following articles are available online (in Wiley InterScience). You can find them at
www.angewandte.org, under Full Text, Early View.
M. Lahav, T. Sehayek, A. Vaskevich, I. Rubinstein*:
Nanoparticle Nanotubes
DOI: 10.1002/anie.200352216
Published online: October 23, 2003
Z. Qin, C. M. Thomas, S. Lee, G. W. Coates*:
Cobalt-Based Complexes for the Copolymerization of Propylene
Oxide and CO2 : Active and Selective Catalysts for Polycarbonate
Synthesis
DOI: 10.1002/anie.200352605
Published online: October 23, 2003
Articles judged by the referees or the editor as being either very important or very urgent are immediately edited, proof-read, and electronically
published once the manuscript has arrived in the editorial office in final form. As long as there is no page number available these articles should be
cited in the following manner:
Author(s) Angew. Chem. Int. Ed., online publication date, DOI.
Web Sites
Malaria: A Parasite Goes Online
Marcel Deponte, Katja Becker-Brandenburg
Cellular Proteins and their Fatty Acids in
Health and Disease
5267
Asim K. Duttaroy, Friedrich Spener
reviewed by Stefan Lorkowski
Chemistry of Crop Protection
G#nther Voss, Gerardo Ramos
reviewed by Jrg Stetter
http://www.sites.huji.ac.il/malaria/ 5266
Books
5267
Highlights
Imaging in NMR Spectroscopy
T. Schulte-Herbr#ggen*
5270 – 5272
Imaging Techniques Boost NMR
Spectroscopy: How To Remove
Zero-Quantum Artifacts
Slicewise excitation, evolution, and
detection are possible by using imaging
techniques in NMR spectroscopy (see
picture). Thus, spatial editing can be
combined with spectral editing, for
example, to remove zero-quantum artifacts from standard NOESY and TOCSY
spectra, as recently described by Keeler
and Thrippleton in this journal.
Reviews
Medicinal Chemistry
J. Wiesner,* R. Ortmann, H. Jomaa,
M. Schlitzer*
5274 – 5293
New Antimalarial Drugs
5256
Increasing resistance of parasites to
established therapeutics has resulted in
malaria remaining one of the unsolved
problems of modern medicine. Current
research concentrates both on new compounds that act through established
mechanisms and on new targets, such as
the farnesyl transferase and the enzymes
of the mevalonate-independent isoprenoid synthesis. (See picture: erythrocyte
infected with P. falciparum.)
2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
Angew. Chem. Int. Ed. 2003, 42, 5256 – 5262
Angewandte
Chemie
Communications
Super Structures: By thermally evaporating elemental layers onto substrates at
ambient temperature, structural precursors are constructed with appropriate
composition and modulation lengths to
kinetically favor the formation of the
desired superstructure. On annealing,
these modulated elemental reactants
form metastable [(Bi2Te3)x(TiTe2)y] superlattices (see picture).
Design and Synthesis of [(Bi2Te3)x(TiTe2)y]
Superlattices
A. Sugawara, T. Ishii,
T. Kato*
5299 – 5303
Self-Organized Calcium Carbonate with
Regular Surface-Relief Structures
Permeable molecular crystals can be specifically designed to let external agents
enter, react, and produce single crystals of
new substances, with retention of the
original crystalline architecture (see picture). Such topotactic processes can be
made to cross-link molecular crystals
covalently, thus capturing temporary
supramolecular constructs as permanent
crystalline macromolecular replicas.
Topotactic Reactions in Networks
P. Brunet, E. Demers, T. Maris,
G. D. Enright, J. D. Wuest* 5303 – 5306
Designing Permeable Molecular Crystals
That React with External Agents To Give
Crystalline Products
Conjugated Schiff-Base Macrocycles
Ion-induced assembly: Supramolecular
structures are obtained in solution by a
new ion-induced assembly of conjugated
Schiff-base macrocycles. A distinct color
change accompanies the aggregation, as
shown in the photo. Shown: Macrocycle (A); with NaBPh4 (B); with KBPh4 (C);
with RbBPh4 (D); with CsBPh4 (E); and
with NH4BPh4 (F) in CH2Cl2.
Angew. Chem. Int. Ed. 2003, 42, 5256 – 5262
F. R. Harris, S. Standridge, C. Feik,
D. C. Johnson*
5296 – 5299
Patterned CaCO3
CaCO3 composites with regular surfacerelief structures have been synthesized
(see picture). These sub-micrometer-scale
structures are spontaneously formed on a
thin matrix of a modified polysaccharide
from aqueous solution containing an
acidic polymer.
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Superlattices
A. J. Gallant,
M. J. MacLachlan*
5307 – 5310
Ion-Induced Tubular Assembly of
Conjugated Schiff-Base Macrocycles
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2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
5257
Contents
Solvent-Induced Chirality Switching
V. V. Borovkov,* G. A. Hembury,
Y. Inoue*
5310 – 5314
The Origin of Solvent-Controlled
Supramolecular Chirality Switching in a
Bis(Zinc Porphyrin) System
Inducing chirality: The supramolecular
interaction of achiral bis(zinc porphyrin)
with enantiopure amino acid derivatives
in different solvents results in chirality
induction. The sign and degree of the
circular dichroims is controlled by the
solvent polarity (see picture).
Microporous Materials
A new dimension to nickel structures: A
three-dimensional nickel glutarate,
[Ni20{(C5H6O4)20(H2O)8}]·40 H2O, has
been prepared under hydrothermal conditions. Its structure, solved from X-ray
powder diffraction, is constructed from
interconnected 20-rings, which form a
remarkable open network of crossing
channels (see picture). It is porous, and
exhibits a ferromagnetic long-range
ordering below 4 K.
N. Guillou,* C. Livage, M. Drillon,
G. FKrey
5314 – 5317
The Chirality, Porosity, and Ferromagnetism of a 3D Nickel Glutarate with Intersecting 20-Membered Ring Channels
Biosensors
E. W. Adams, J. Ueberfeld, D. M. Ratner,
B. R. O’Keefe, D. R. Walt,*
P. H. Seeberger*
5317 – 5320
Encoded Fiber-Optic Microsphere Arrays
for Probing Protein–Carbohydrate
Interactions
Zinc Oxide Nanoparticles
M. Monge, M. L. Kahn, A. Maisonnat,
B. Chaudret*
5321 – 5324
Room-Temperature Organometallic
Synthesis of Soluble and Crystalline ZnO
Nanoparticles of Controlled Size and
Shape
5258
Protein–carbohydrate interactions can be
evaluated by using randomly ordered fiber
optic microsphere arrays bearing immobilized synthetic oligosaccharides (see
scheme). Two systems are examined: the
mannose-binding lectin concanavalin A,
and cyanovirin N. The latter allows the
simultaneous evaluation of five distinct
structures against a carbohydrate-binding
protein with unambiguous results.
Nanomaterials made easy! The facile
oxidation of [Zn(c-C6H11)2] at room temperature in an organic solvent containing
long-chain amine ligands leads to the
formation of size- and shape-controlled
crystalline ZnO nanoparticles (see picture). These particles, in the form of
nanodisks and nanorods of low size
dispersity in the 3–10 nm size range, are
fully soluble in organic solvents (e.g.,
THF) and photoluminescent.
2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
Angew. Chem. Int. Ed. 2003, 42, 5256 – 5262
Angewandte
Chemie
Stabilizing the gp41 Trimer in HIV-1
M. Gochin,* R. Kiplin Guy,
M. A. Case
A stable fragment of the HIV-1 gp41 inner
coiled coil has been designed. The addition of a transition-metal ion to bipyridylated gp41 peptides stabilizes the trimeric
helical structure of the coiled coil through
the formation of an octahedral tris-bipyridyl complex, and removes nonspecific
aggregation of the hydrophobic peptide
(see picture). The resulting structure
recognizes peptides known to bind to the
viral coiled coil and was used to develop a
simple, useful and sensitive assay to
rapidly detect binding of potential fusioninhibiting drugs.
5325 – 5328
A Metallopeptide Assembly of the HIV-1
gp41 Coiled Coil Is an Ideal Receptor in
Fluorescence Detection of Ligand Binding
Carbon-Rich Compounds
An insoluble disclike building block
hexa(4-iodophenyl)-peri-hexabenzocoronene (see picture) was synthesized in an
efficient way, and subsequent functionalization led to a series of soluble, star-type
hexabenzocoronenes (HBCs), all showing
remarkable self-assembly behavior:
1) highly ordered liquid-crystalline
materials, 2) dendronized HBCs, and
3) triarylamine-substituted HBCs.
J. Wu, M. D. Watson,
K. M#llen*
5329 – 5333
The Versatile Synthesis and Self-Assembly
of Star-Type Hexabenzocoronenes
Chemoselective Hydrogenation
M. De bruyn, S. Coman, R. Bota,
V. I. Parvulescu, D. E. De Vos,
P. A. Jacobs*
5333 – 5336
The combination of Ir, which has a strong
affinity for carbonyl groups, with an acid
H-b zeolite as a support and promotor,
provides an effective catalyst for the
chemoselective hydrogenation of a,b-
Angew. Chem. Int. Ed. 2003, 42, 5256 – 5262
unsaturated aldehydes and ketones to the
corresponding allylic alcohols. Steroidal
enones are suitable substrates for this
transformation (see scheme).
R = CH(Me)(CH2)3CH(Me)2.
Chemoselective Reduction of Complex
a,b-Unsaturated Ketones to Allylic Alcohols over Ir-Metal Particles on b Zeolites
Theophilline-imprinted polymer microspheres were obtained in monodisperse
form with diameters of about 5 mm (see
picture) in a single synthetic step by
precipitation polymerization. This robust
material, which proved suitable for use in
HPLC, can, in principle, also be applied in
any application in which molecular
recognition phenomena play a role.
Imprinted Polymer Microspheres
www.angewandte.org
J. Wang, P. A. G. Cormack,*
D. C. Sherrington,
E. Khoshdel
5336 – 5338
Monodisperse, Molecularly Imprinted
Polymer Microspheres Prepared by
Precipitation Polymerization for Affinity
Separation Applications
2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
5259
Contents
trans Diamine PtII Anticancer Complex
A. M. Pizarro, V. P. Munk,
C. Navarro-Ranninger,
P. J. Sadler*
5339 – 5342
Hydrolysis Triggers Oxidation of a trans
Diamine Platinum(ii) Anticancer Complex
1
H, 15N and 195Pt NMR spectroscopy
experiments show that the aqua adducts
of a trans diamine platinum(ii) anticancer
complex unexpectedly undergo facile
oxidation to platinum(iv) in aqueous
solution in air (see picture).
Facial stereocontrol is possible in Michael
additions of nucleophiles (Nu) to alkylidene bis(sulfoxides), which proceed via
nonchelated (A) or chelated (B) intermediates depending on the addition of an
appropriate Lewis acid (LA). This intriguing reactivity could be applied to the first
total synthesis of the succinate-based
natural product, (þ)-erythro-roccellic acid.
Aromatic CH silylation of arenes by 1,2di-tert-butyl-1,1,2,2-tetrafluorodisilane is
efficiently catalyzed by iridium(i) complexes generated from [{Ir(OMe)(cod)}2]
(cod = cyclooctadiene) and 4,4’-di-tertbutyl-2,2’-bipyridine (dtbpy; see scheme)
and provides the corresponding aryl
fluorosilanes in excellent yields.
Stereoselective Conjugate Addition
F. Brebion, B. DelouvriK, F. NSjera,
L. Fensterbank,* M. Malacria,*
J. Vaissermann
5342 – 5345
Highly Diastereoselective Conjugate
Addition to Alkylidene Bis(Sulfoxides):
Asymmetric Synthesis of
(þ)-erythro-Roccellic Acid
Ir-Catalyzed Silylation of Arenes
T. Ishiyama,* K. Sato, Y. Nishio,
N. Miyaura*
5346 – 5348
Direct Synthesis of Aryl Halosilanes
through Iridium(i)-Catalyzed Aromatic
CH Silylation by Disilanes
Hexapeptide Total Synthesis
J. Zhu, D. Ma*
5348 – 5351
Total Synthesis of Microsclerodermin E
5260
Succumbing to total synthesis: Microsclerodermin E, a 23-membered cyclic
hexapeptide possessing antifungal activity, has been prepared for the first time.
Key features in the synthesis include the
construction of four unusual amino acid
units, the assembly of the pyrrolidinone
fragment with little racemization, and an
effective macrocyclization.
2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
Angew. Chem. Int. Ed. 2003, 42, 5256 – 5262
Angewandte
Chemie
Natural Products Total Synthesis
Ketal isomers avoided. The unique 2,8dioxabicyclo[3.2.1]octane core of zaragozic acid C (1) was constructed in a Rhcatalyzed 1,3-dipolar cycloaddition of an
alkyne to an ester carbonyl ylide. Another
feature of this improved synthesis is the
construction of the alkyl side chain at C1
by olefin cross-metathesis.
S. Nakamura, Y. Hirata, T. Kurosaki,
M. Anada, O. Kataoka, S. Kitagaki,
S. Hashimoto*
5351 – 5355
Total Synthesis of the Squalene Synthase
Inhibitor Zaragozic Acid C by a Carbonyl
Ylide Cycloaddition Strategy
Iron-Catalyzed Allenol Formation
A. F#rstner,* M. MKndez
Reliable chirality transfer is one of the
major advantages of a novel synthesis of
2,3-allenols from propargyl epoxides (see
scheme) catalyzed by inexpensive and
environmentally benign iron salts. The
reactions proceed very rapidly in excellent
yields and with moderate to good
diastereoselectivity in favor of the
syn-configured product.
5355 – 5357
Iron-Catalyzed Cross-Coupling Reactions:
Efficient Synthesis of 2,3-Allenol
Derivatives
Natural Product Synthesis
The highly selective actin-binding latrunculins (e.g. 1) play a prominent role as
probe molecules in chemical biology. A
highly concise, productive, and inherently
flexible approach to 1 illustrates the
excellent profile and use of metal-catalyzed CC bond formations.
A. F#rstner,* D. De Souza,
L. Parra-Rapado, J. T. Jensen 5358 – 5360
Catalysis-Based Total Synthesis of
Latrunculin B
The unexpected selectivity profile of
(17R)- and (17S)-TMC-69-6H (see formula) suggests that N-hydroxypyridone
derivatives constitute a promising new
lead structure in the search for selective
phosphatase inhibitors. An unprecedented Pd-catalyzed CC bond formation
to a pyranone derivative was a key step in
the synthesis of enantiopure
(17R)- and (17S)-TMC-69-6H.
Phosphatase Inhibitors
A. F#rstner,* F. Feyen, H. Prinz,
H. Waldmann
5361 – 5364
Total Synthesis and Reassessment of the
Phosphatase-Inhibitory Activity of the
Antitumor Agent TMC-69-6H
Communications labeled with this symbol have been judged by two referees as being “very important papers”.
The publication of Communications labeled with this symbol has been accelerated because of their topical or highly competitive
nature.
Angew. Chem. Int. Ed. 2003, 42, 5256 – 5262
www.angewandte.org
2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
5261
Contents
Service
Keywords
5366
Authors
5367
Preview
5369
Corrigendum
*
In the Communication “Equilibrium and
Kinetic Deuterium Isotope Effects on the
Hetero-Diels–Alder Addition of Sulfur
Dioxide” by P. Vogel, J. A. Sordo et al.
(Angew. Chem. Int. Ed 2003, 42, 3924–
3927), lines 7 and 11 as well as lines 8 and
12 of Table 2 (pg. 3926) have been swapped. The correct table is shown below:
Table 2: Calculated kinetic deuterium isotope effect for concerted hetero-Diels–Alder additions.
75
T [8C]
54
+ 25
0.692
(0.714)
0.776
(0.734)
1.12
0.725
(0.746)
0.801
(0.763)
1.10
0.816[b]
(0.830)[c]
0.869[b]
(0.841)[c]
1.06
0.707
(0.721)
0.748
(0.755)
0.693
(0.673)
0.658
(0.647)
0.741
(0.754)
0.780
(0.785)
0.729
(0.709)
0.695
(0.685)
0.829[b]
(0.842)[c]
0.861[f ]
(0.865)[g]
0.824[b,j]
(0.806)[c,k]
0.796[f ]
(0.789)[g]
Reaction
[a]
1/3 + 2 SO2 ![11]!4 + SO2
kH/kD
1/3 + 2 SO2 ![12]!5 + SO2
k0H/k0D[d]
Kinetic regioselectivity:[i]
Ratio
15/16 + 2 SO2 ![11’]!4’ + SO2
kH/kD[e]
15/16 + 2 SO2 ![12’]!5’ + SO2
k0H/k0D[h]
[a] kH/kD =
^ k1/2 k4. [b] B3LYP/6-31G(d). [c] B3LYP/6-31G(d) for the reaction with only one equivalent
of SO2. [d] k0H/k0D =
^ k1/2 k5. [e] kH/kD =
^ butadiene + 2 SO2 vs. 1,1-D2-butadiene + 2 SO2 giving a
sultine analogous to 4. [f] MP2/6-31G(d). [g] MP2/6-31G(d) for the reaction with only one
^ butadiene + 2 SO2 vs. 1,1-D2-butadiene + 2 SO2 giving sultine
equivalent of SO2. [h] k0H/k0D =
analogous to 5. [i] k0H/k0D(5)/kH/kD(4); calculated (B3LYP/6-31G(d) including zero-point energy).
[j] Energy barrier: 4.8 kcal mol1. [k] Energy barrier: 12.2 kcal mol1.
5262
2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
Angew. Chem. Int. Ed. 2003, 42, 5256 – 5262
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