A Submarine Journey: The Pyrrole-Imidazole Alkaloids

被引：206

作者：

Forte, Barbara ^{[1
]}

Malgesini, Beatrice ^{[2
]}

Piutti, Claudia ^{[1
]}

Quartieri, Francesca ^{[2
]}

Scolaro, Alessandra ^{[1
]}

Papeo, Gianluca ^{[1
]}

机构：

[1] Nerviano Med Sci, Dept Med Chem, I-20014 Milan, Italy

[2] Nerviano Med Sci, Dept Chem Core Technol, I-20014 Milan, Italy

来源：

MARINE DRUGS | 2009年 / 7卷 / 04期

关键词：

pyrrole-imidazole alkaloids; total synthesis; marine sponges; oroidin; ENANTIOSELECTIVE TOTAL-SYNTHESIS; SPONGE AGELAS-DENDROMORPHA; PUMMERER REACTION CHEMISTRY; MARINE NATURAL-PRODUCTS; BROMOPYRROLE ALKALOIDS; A-D; MATRIXMETALLOPROTEINASE INHIBITOR; RELATIVE CONFIGURATION; ABSOLUTE-CONFIGURATION; BIOSYNTHETIC PRECURSOR;

D O I：

10.3390/md7040705

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

In his most celebrated tale "The Picture of Dorian Gray", Oscar Wilde stated that "those who go beneath the surface do so at their peril". This sentence could be a prophetical warning for the practitioner who voluntarily challenges himself with trying to synthesize marine sponge-deriving pyrrole-imidazole alkaloids. This now nearly triple-digit membered community has been growing exponentially in the last 20 years, both in terms of new representatives and topological complexity - from simple, achiral oroidin to the breathtaking 12-ring stylissadines A and B, each possessing 16 stereocenters. While the biosynthesis and the role in the sponge economy of most of these alkaloids still lies in the realm of speculations, significant biological activities for some of them have clearly emerged. This review will account for the progress in achieving the total synthesis of the more biologically enticing members of this class of natural products.

引用

页码：705 / 753

页数：49

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