“…One can envision an 11,12-dehydrophakellin, itself derived from pyrrole-2-carboxylic acid and AAPE, plus a second equivalent of AAPE undergoing a Diels−Alder reaction, followed by a chloroperoxidase-initiated chlorination, bond migration, and reaction with water, as shown in Scheme and confirmed by synthesis 1 …”
The strongly cytotoxic, antibiotic, and immunosuppressive palau'amine was isolated from the Belau sponge Stylotella aurantium, along with less active 4-bromo and 4,5-dibromo derivatives. Three corresponding isomeric compounds, all less active, were also isolated, and full details of the isolation and all structure proofs are provided.
“…One can envision an 11,12-dehydrophakellin, itself derived from pyrrole-2-carboxylic acid and AAPE, plus a second equivalent of AAPE undergoing a Diels−Alder reaction, followed by a chloroperoxidase-initiated chlorination, bond migration, and reaction with water, as shown in Scheme and confirmed by synthesis 1 …”
The strongly cytotoxic, antibiotic, and immunosuppressive palau'amine was isolated from the Belau sponge Stylotella aurantium, along with less active 4-bromo and 4,5-dibromo derivatives. Three corresponding isomeric compounds, all less active, were also isolated, and full details of the isolation and all structure proofs are provided.
“…Shortly after its isolation, synthetic efforts by Ahond and Commerc ¸on led to the elucidation of the absolute configuration of girolline. 57 In his approach Commerc ¸on 58 employed an Evans' aldol strategy to establish the chlorohydrin relative and absolute stereochemistry (i.e. chlorohydrin 77, Scheme 16).…”
The pyrrole-2-aminoimidazole (P-2-AI) alkaloids are a growing family of marine alkaloids, now numbering well over 150 members, with high topographical and biological information content. Their intriguing structural complexity, rich and compact stereochemical content, high N to C ratio (~1:2), and increasingly studied biological activities are attracting a growing number of researchers from numerous disciplines world-wide. This review surveys advances in this area with a focus on the structural diversity, biosynthetic hypotheses with increasing but still rare verifying experimental studies, asymmetric syntheses, and biological studies including cellular target receptor isolation studies of this stimulating and exciting alkaloid family.
“…Studies performed on the crude ethanol extracts of C. cantharella led to the isolation of girolline ( 7 , Figure 5 B). Its absolute configuration has been established by X-ray diffraction [ 56 ] and total synthesis was achieved few years later [ 53 , 57 , 58 , 63 , 100 ].…”
Marine micro- and macroorganisms are well known to produce metabolites with high biotechnological potential. Nearly 40 years of systematic prospecting all around the New Caledonia archipelago and several successive research programs have uncovered new chemical leads from benthic and planktonic organisms. After species identification, biological and/or pharmaceutical analyses are performed on marine organisms to assess their bioactivities. A total of 3582 genera, 1107 families and 9372 species have been surveyed and more than 350 novel molecular structures have been identified. Along with their bioactivities that hold promise for therapeutic applications, most of these molecules are also potentially useful for cosmetics and food biotechnology. This review highlights the tremendous marine diversity in New Caledonia, and offers an outline of the vast possibilities for natural products, especially in the interest of pursuing collaborative fundamental research programs and developing local biotechnology programs.
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