Mini-Reviews in Organic Chemistry, Volume 2, No. 2, 2005
Contents
Bacterial Citrate Siderophores Pp.119-124
Organic Chemistry in Ionic Liquids Using
Non-Thermal Energy-Transfer Processes Pp.125-137
Jorg Habermann, Simona
Ponzi and Steven V. Ley
The Furan-2(5H)-ones: Recent Synthetic
Methodologies and its Application in Total Synthesis of Natural Products Pp.139-145
Marcus Vinicius Nora
De Souza
Utilization of Phenyl Trialkylstannyl Selenide
as a Promising Reagent for Introduction of the Phenylseleno Group Pp.147-155
Yutaka Nishiyama and
Noboru Sonoda
Synthesis of Acylnitroso Intermediates and
Their Synthetic Applications Pp.157-175
Seiji Iwasa, Ahmad
Fakhruddin and Hisao Nishiyama
Recent Advances in Rare Earth-Metal Triflate
Catalyzed Organic Synthesis in Green Media Pp.177-202
Sanzhong Luo, Lizhi Zhu,
Arindam Talukdar, Guisheng Zhang, Xueling Mi, Jin-Pei Cheng and Peng George
Wang
Abstracts
[Back to top] Bacterial Citrate Siderophores
H. Budzikiewicz
Soil bacteria as well as those infecting
other organisms have developed systems to secure iron necessary for their
metabolism which is generally not available in its free ionic form. As one of
the possible strategies they learnt to produce secondary metabolites able to
bind Fe3+ as water soluble complexes, so-called siderophores. A
rather small group is based on citric acid. One of the ligand sites is the
central C(OH)COOH unit, the two additional ones are carried by substituents
bound to one or both of the terminal carboxyl groups. A survey will be
presented.
[Back to top] Organic Chemistry in Ionic Liquids Using
Non-Thermal Energy-Transfer Processes
Jorg Habermann, Simona
Ponzi and Steven V. Ley
As a result of the chemical industry being
under pressure to reduce its usage of volatile solvents ionic liquids are of
considerable interest as environmentally benign solvents for organic synthesis
programs. Isolation of products is generally facilitated by the fact that ionic
liquids form biphasic systems with many organic product mixtures. Recent
research has emphasised the use of ionic liquids as solvents and co-solvents in
reaction conditions requiring non-thermal heating processes since their ionic
nature makes them susceptible to interaction with electromagnetic fields
(heating by microwave irradiation). Furthermore, their low vapour pressure
allows high temperatures to be reached and leads to interesting behaviour
during ultrasound promoted reactions.
[Back to top] The Furan-2(5H)-ones: Recent Synthetic
Methodologies and its Application in Total Synthesis of Natural Products
Marcus Vinicius Nora
De Souza
In recent years, furan-2(5H)-ones have
attracted considerable attention as synthetic target. This subunit is present
in a large number of natural products, which display a wide range of biological
activities, and is present in a number of drugs with diverse biological
activities, such as antifungal, antibacterial and anti-inflammatory. It can also
be used as synthetic intermediate. This review describes recent synthetic
methodologies for preparation of furan-2(5H)-ones, as well as their
application in the total synthesis of natural products with this subunit.
[Back to top] Utilization of Phenyl Trialkylstannyl Selenide as
a Promising Reagent for Introduction of the Phenylseleno Group
Yutaka Nishiyama and Noboru Sonoda
New synthetic methods of organoselenium
compounds by the use of phenyl tributylstannyl selenide (PhSeSnBu3)
(1), which is a stable selenium reagent in air and moisture, as a
phenylselenated reagent have been developed. In the presence of palladium
complex catalyst, the reaction of 1 with organohalogen compounds took place
efficiently to give the corresponding organoselenium compounds in moderate to
good yields. Furthermore, it was found that Lewis acid assisted the reaction of
1 with oxygen-containing compounds giving the corresponding organoselenium
compounds.
[Back to top] Synthesis of Acylnitroso Intermediates and
Their Synthetic Applications
Seiji Iwasa, Ahmad
Fakhruddin and Hisao Nishiyama
Acylnitroso intermediates are usually known
as super reactive species, always prepared in situ and can be readily
trapped via hetero-Diels-Alder reactions with dienes or with olefins via
ene reactions, which open a magnificent access to produce a variety of
complicated and very demanding organic molecules. Both of these reactions of
acylnitroso species have been proved as the key synthetic tool in the total
synthesis of natural products. The synthetic methods used to prepare these
intermediates as well as their recent synthetic applications to the total
synthesis of natural products are briefly described in this minireview.
[Back to top] Recent Advances in Rare Earth-Metal Triflate
Catalyzed Organic Synthesis in Green Media
Sanzhong Luo, Lizhi
Zhu, Arindam Talukdar, Guisheng Zhang, Xueling Mi, Jin-Pei Cheng and Peng
George Wang
Rare-earth metal triflates have been well
established as potent environmentally-benign Lewis acids. This review
summarizes the recent progress of RE(OTf)3 catalyzed organic
synthesis in green media including water, ionic liquids, super critical CO2,
solvent-free conditions as well as solid supported synthesis.