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Current Organic Synthesis
ISSN: 1570-1794
Current Organic Synthesis
Volume 3, Number 3, August 2006
Contents
Synthesis of 2',3'-Didehydro-2',3'-dideoxynucleosides
via Nucleoside Route Pp. 261-281
Christophe Len and Denis Postel
[Abstract]
Synthesis of Bicyclic Peptides Pp. 283-311
Tuomas Karskela, Pasi Virta and Harri Lönnberg
[Abstract]
Stille Reaction: An Important Tool in the Synthesis
of Complex Natural Products Pp. 313-326
Marcus Vinícius Nora De Souza
[Abstract]
Natural Products Bearing a Bicyclo[3.2.0]Heptane Skeleton
Pp. 327-340
Michel Miesch
[Abstract]
Chemistry and Synthesis of Highly Oxygenated Alkaloids
from Amaryllidaceae: Lycoricidine, Narciclasine, Pancratistatin
and Analogs Pp. 341-378
Y. Chapleur, F. Chrétien, S. Ibn Ahmed and M. Khaldi
[Abstract]
The Chemistry of Anthranilic Acid Pp. 379-402
Per Wiklund and Jan Bergman
[Abstract]
Abstracts
[Back to top]
Synthesis of 2',3'-Didehydro-2',3'-dideoxynucleosides
via Nucleoside Route
Christophe Len and Denis Postel
2',3'-Didehydro- and 2',3'-dideoxynucleosides are both potent
antiviral agents. In particular, they are Nucleoside Reverse
Transcriptase Inhibitors and hence active against HIV, the
ethiological agent of AIDS. They are also intermediates for
the synthesis of antiviral 2',3'-dideoxynucleosides. Various
aspects of synthetic routes to 2',3'-unsaturated nucleosides
are reviewed with examples being chosen from work published
between 1966 and 2003.
[Back to top]
Synthesis of Bicyclic Peptides
Tuomas Karskela, Pasi Virta and Harri Lönnberg
Bicyclic peptides have received interest as anticancer agents,
protease inhibitors, antibiotics, receptor antagonists, artificial
receptors and models of various structural motives of proteins.
Their common characteristic feature, limited conformational
freedom of the backbone, plays a central role in all these
applications. The same feature poses a challenge for synthetic
organic chemists. Additional levels have to be included in
the protecting group strategy to ensure the desired regioselectivity
of cyclization and still the yields tend to be low, owing
to increasing rigidity that cyclizations, in particular the
second one, result in. The present review is aimed at summarizing
the strategies described for the synthesis of various types
of bicyclic peptides, originally in solution-phase and nowadays
more often on a solid-support.
[Back to top]
Stille Reaction: An Important Tool in the Synthesis
of Complex Natural Products
Marcus Vinícius Nora De Souza
Nowadays, palladium-catalysed coupling reactions are one of
the most efficient procedures for the construction of C-C
bonds. In this context, a reaction that is known as Stille
reaction, published in 1978 by J. K. Stille and D. Milstein,
is a powerful tool in the modern total synthesis. This reaction
is based in organotin compounds and catalytic amount of palladium
complexes, which in high yields and mild conditions allowed
the synthesis of different complex natural and non-natural
biologically active compounds, as well synthetic key intermediates.
The aim of this review is to highlight the Stille reaction
as a very important procedure in the synthesis of some complex
natural products accomplished between 2000 and 2004.
[Back to top]
Natural Products Bearing a Bicyclo[3.2.0]Heptane Skeleton
Michel Miesch
This first part of this article focuses on natural products
bearing a bicyclo[3.2.0]heptane skeleton. The second part
deals with the synthesis of such natural products by focusing
on the formation of the bicycloheptane substructure.
[Back to top]
Chemistry and Synthesis of Highly Oxygenated Alkaloids
from Amaryllidaceae: Lycoricidine, Narciclasine, Pancratistatin
and Analogs
Y. Chapleur, F. Chrétien, S. Ibn Ahmed and M. Khaldi
Plants of the genus Amaryllidaceae produce a number of alkaloids
and other non-basic related molecules, some of them showing
antitumor activities. The low availability of these often-complex
structures, coupled with their interesting biological properties,
has stimulated a long-standing interest in the chemistry community.
Total syntheses of challenging structures such as lycoricidine,
narciclasine and pancratistatin, which are highly oxygenated
tetracyclic systems comprising up to six contiguous chiral
centers on ring C, have been accomplished. These well-known
structures, more than thirty years for lycoricidine, continue
to stimulate interest in synthetic work to provide enough
synthetic material or analogs, and also are a model target
to test or develop new synthetic methodologies. The synthetic
studies around these complex phenanthridinones made use of
the latest up-to-date synthetic methodologies and led to the
development of novel methods of functionalization and carbon-carbon
bond formation. The purpose of this review is to summarize
recent total syntheses and synthetic approaches towards these
three highly oxygenated members of this particular class of
alkaloids over the last twenty years. The review is arranged
according to the different strategies used for the construction
of the benzophenanthridinone ring system.
[Back to top]
The Chemistry of Anthranilic Acid
Per Wiklund and Jan Bergman
Anthranilic acid (2-aminobenzoic acid, AA) is a versatile
and low cost starting material for synthesis of benzofused
heterocycles. It also plays a vital part in the biosynthesis
of tryptophan and its derivatives, as well as in several types
of alkaloids. Therefore the chemistry of anthranilic acid
is of importance in medicinal and biological chemistry. The
main emphasis of this review article is on the use of anthranilic
acid as a starting material for synthesis of heterocycles,
but it also covers the history, synthesis and reactivity,
as well as a short account of the medicinal chemistry and
biochemistry of anthranilic acids.
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