Isolation, biological activity, synthesis, and medicinal chemistry of the pederin/mycalamide family of natural products

Abstract

This review highlights the broad range of science that has arisen from the isolation of pederin, the mycalamides, theopederins, and onnamides, and psymberin. Specific topics include structure determination, biological activity, synthesis, and analog preparation and analysis.

Predominately Uncultured Microbes as Sources of Bioactive Agents

“…Representative examples of these compounds have been synthesized by considerable numbers of organic chemists in the last 10 plus years. The following papers should be consulted by readers interested in the synthetic processes used (Jewett and Rawal, 2007; Jiang et al, 2007; Nishii et al, 2009; Wan et al, 2011; Wu et al, 2011, 2012; Mosey and Floreancig, 2012; Floreancig, 2014; Uesugi et al, 2015). Of these, the review by Mosey and Floreancig (2012) gives a relatively thorough overview of the isolation, biological activities, and medicinal chemistry of these agents.…”

Natural Products as Pharmaceuticals and Sources for Lead Structures**Note: This chapter reflects the opinions of the authors, not necessarily those of the US Government

“…Further examples of the unusual molecules produced by extremophilic microbes can be seen from the work reported by the Lin group on spiromastixones A-O from a deep sea fungus [80], the discussion on bioactive natural products from cold seas by Liu et al [81], the review by Mosey and Floreancig on the pederin/mycalamide family [82],-which should be read in conjunction with the work reported later by the Piel group-and the very recent and excellent review covering reports from 2009 to 2013 by Skropeta and Wei on recent advances in deep-sea natural products [83].…”

Re2O7‐Mediated Dehydrative Cyclization Reactions: Total Synthesis of Herboxidiene and Its 12‐Desmethyl Analogue

“…The compatibility of the nitro group provides an entry to structures in which amino acids are incorporated into polyketide biosynthetic pathways. [15] Matching (entry 8) or mismatching influences (entry 9) dictate the degree of stereocontrol when two non-equilibrating stereocenters are present in the substrate.…”