The chemistry of isoindole natural products

Abstract

SummaryThis review highlights the chemical and biological aspects of natural products containing an oxidized or reduced isoindole skeleton. This motif is found in its intact or modified form in indolocarbazoles, macrocyclic polyketides (cytochalasan alkaloids), the aporhoeadane alkaloids, meroterpenoids from Stachybotrys species and anthraquinone-type alkaloids. Concerning their biological activity, molecular structure and synthesis, we have limited this review to the most inspiring examples. Within different congeners, we have selected a few members and discussed the synthetic routes in more detail. The putative biosynthetic pathways of the presented isoindole alkaloids are described as well.

Development of Halogenase Enzymes for Use in Synthesis

“…122 Figure 15A). [161][162][163] The peptidyl carrier protein (PCP) tethered substrates of Clz5, PltA and HalB are all derived from oxidation of proline-S-PCP intermediates in NRPS or NRPS-PKS assembly lines. Genome mining of the marine organisms responsible for the biosynthesis of brominated marine natural products has led to the identification of an interesting pyrrole Fl-Hal, Bmp2, from…”

Synthesis and Reduction of 10-Phthalimidocamphor Oxime

“…Isoindolinone/isoindole derivatives can be found in numerous natural and pharmaceutical compounds shoving multiple biological activities ( Figure 1). 25 …”

1,3-Dipolar cycloaddition reactions of azomethine ylides with aromatic dipolarophiles

“…[42][43][44] The isoindole framework is found within a large range of natural products and frequently features in bioactive natural products, synthetic agrochemicals, pharmaceuticals and dyes. [45][46][47] Although simple and elegant in concept, azomethine ylide 1,3-dipolar cycloaddition dearomatization processes have received only sporadic attention until recently. 45 Here is presented a comprehensive review of the literature associated with the 1,3-dipolar cycloaddition reactions of azomethine ylides with benzo-and heteroaromatic systems until the end of 2013.…”

“…[45][46][47] Although simple and elegant in concept, azomethine ylide 1,3-dipolar cycloaddition dearomatization processes have received only sporadic attention until recently. 45 Here is presented a comprehensive review of the literature associated with the 1,3-dipolar cycloaddition reactions of azomethine ylides with benzo-and heteroaromatic systems until the end of 2013. While outside the scope of this review, it is noted that the cycloaddition of azomethine ylides to C 60 , graphite and related materials is considered an excellent way to functionalize these materials.…”