Mini-Reviews in Organic Chemistry, Volume 2, No. 3, 2005
Contents
Is Circularly Polarized Light an Effective
Reagent For Asymmetric Synthesis? Pp.203-209
Richard M. Pagni and
Robert N. Compton
The Synthesis of Aplysinopsins, Meridianines,
and Related Compounds
Pp.211-224
Branko Stanovnik and
Jurij Svete
Cyclohexane-Based Conformationally Controlled
Crowns and Podands
Pp.225-235
Vyacheslav V. Samoshin
Cyclodextrins in Nitrosation Chemistry: New Insights
of the NO-Transfer Processes
Pp.237-263
Emilia Iglesias
Lipases-Promoted Enantioselective Syntheses
of Monocyclic Natural Products
Pp.265-281
Honore Monti and
Gerard Audran
Carbohydrate-Derived Surfactants Pp.283-297
Mauro Vieira de
Almeida and Mireille Le Hyaric
Abstracts
[Back to top] Is Circularly Polarized Light an Effective Reagent
For Asymmetric Synthesis?
Richard M. Pagni and
Robert N. Compton
Photoreactions initiated with circularly
polarized light (CPL), which exists in left-handed and right-handed forms and
is easy to prepare, has had limited success in asymmetric synthesis although
they may model the pre-biotic origin of optically active molecules on the
earth. Other approaches including multiphoton excitation with CPL may prove
more successful in asymmetric synthesis.
[Back to top] The Synthesis of Aplysinopsins, Meridianines,
and Related Compounds
Branko Stanovnik and
Jurij Svete
Aplysinopsins and meridianines have been
isolated from various marine organisms. They exhibit interesting biological
activity, such as cytotoxicity and neurotransmission effects. Various synthetic
approaches towards these two classes of natural products and their synthetic
analogs have been developed. Most syntheses of aplysinopsins, meridianines, and
their analogs are based either on coupling of two heterocyclic moieties via
the methylidene bridge, or on heterocyclization of indoles, functionalized at
position 3.
[Back to top] Cyclohexane-Based Conformationally Controlled
Crowns and Podands
Vyacheslav V. Samoshin
Cyclohexane-based conformationally controlled
ionophores, the emerging new class of molecular switches, provide a new and
promising approach to allosteric systems with negative cooperativity.
[Back to top] Cyclodextrins in Nitrosation Chemistry: New
Insights of the NO-Transfer Processes
Emilia Iglesias
The chemistry of nitroso compounds has
received considerable attention from several directions in recent years. This
review will focus on describing the practical aspects, and current and
potential applications of cyclodextrins in mechanistic studies of NO-transfer
processes. The first section describes some physico-chemical aspects of aqueous
cyclodextrin solutions that are of crucial importance in relation to
mechanistic studies. The next section analyses all types of information that
can be obtained from different nitrosation reaction patterns either in acid or
basic media, by paying special attention to the nitrosatable substrates and
nitrosating agents. Relevant aspects concerning the biological activity of
nitroso compounds is also included. The last section covers a detailed analysis
of the effects of cyclodextrins on reactions undergone by nitroso compounds,
such as hydrolysis or NO-transfer, as well as on reactions that produce nitroso
compounds.
[Back to top] Lipases-Promoted Enantioselective Syntheses
of Monocyclic Natural Products
Honore Monti and
Gerard Audran
This review is about using lipases as
catalysts in organic synthesis. It provides some specific examples of
stereoselective biotransformations used in our group to prepare non racemic
chiral building blocks and the utilization of these intermediates to synthesize
different target molecules by organic transformations.
[Back to top] Carbohydrate-Derived Surfactants
Mauro Vieira de
Almeida and Mireille Le Hyaric
The constant need for products obtained from
natural raw materials instead of non-renewable petroleum feedstocks has led to a
lot of effort on developing new “natural” surfactants. Most important among
these are surfactants derived from carbohydrates and plant oils such as coconut
or palm kernel. These compounds find applications in cosmetics, food
manufacture, biology, etc, and some of them are studied for their liquid
crystalline properties.