Extraction, Isolation, Characterization, and Bioactivity of Polypropionates and Related Polyketide Metabolites from the Caribbean Region.

The Caribbean region is a hotspot of biodiversity (i.e., algae, sponges, corals, mollusks, microorganisms, cyanobacteria, and dinoflagellates) that produces secondary metabolites such as polyketides and polypropionates. Polyketides are a diverse class of natural products synthesized by organisms through a biosynthetic pathway catalyzed by polyketide synthase (PKS). This group of compounds is subdivided into fatty acids, aromatics, and polypropionates such as macrolides, and linear and cyclic polyethers. Researchers have studied the Caribbean region to find natural products and focused on isolation, purification, structural characterization, synthesis, and conducting biological assays against parasites, cancer, fungi, and bacteria. These studies have been summarized in this review, including research from 1981 to 2020. This review includes about 90 compounds isolated in the Caribbean that meet the structural properties of polyketides. Out of 90 compounds presented, 73 have the absolute stereochemical configuration, and 82 have shown biological activity. We expect to motivate the researchers to continue exploring the Caribbean region's marine environments to discover and investigate new polyketide and polypropionate natural products.

Epoxide-Based Synthetic Approaches toward Polypropionates and Related Bioactive Natural Products.

Polypropionate units are a common structural feature of many of the natural products in polyketides, some of which have shown a broad range of antimicrobial and therapeutic potential. Polypropionates are composed of a carbon skeleton with alternating methyl and hydroxy groups with a specific configuration. Different approaches have been developed for the synthesis of polypropionates and herein we include, for the first time, all of the epoxide-based methodologies that have been reported over the years by several research groups such as Kishi, Katsuki, Marashall, Miyashita, Prieto, Sarabia, Jung, McDonald, etc. Several syntheses of polypropionate fragments and natural products that employed epoxides as key intermediates have been described and summarized in this review. These synthetic approaches involve enatio- and diastereoselective synthesis of epoxides (epoxy-alcohols, epoxy-amides, and epoxy-esters) and their regioselective cleavage with carbon and/or hydride nucleophiles. In addition, we included a description of the isolation and biological activities of the polypropionates and related natural products that have been synthetized using epoxide-based approaches. In conclusion, the epoxide-based methodologies are a non-aldol alternative approach for the construction of polypropionate.