Indolylvinyl Ketones: Building Blocks for the Synthesis of Natural Products and Bioactive Compounds

Abstract

Indolylvinyl ketones are valuable building blocks that can be utilized for the synthesis of numerous natural products and bioactive molecules containing an indole core motif. Herein, we describe their application for the total synthesis of some alkaloids, their analogues, and a variety of other important compounds, with an emphasis on biologically active examples.1 Introduction2 Functionalization of the Enone C=C Bond2.1 Reduction2.2 Michael Addition2.3 Cycloaddition3 Transformation of the Carbonyl Group3.1 Reduction3.2 Knoevenagel Reaction3.3 Addition of Organometallic Compounds3.4 Olefination4 Reactions Involving the Enone Conjugate System С=С–С=О4.1 Reactions with 1,2-Dinucleophiles4.2 Reactions with Compounds Bearing an Active Methylene Group4.3 Reactions with 1,3-Dinucleophiles4.4 Reactions with 1,4-Dinucleophiles5 Functionalization of the Enone Methylene Group C(O)–CH2R5.1 Acylation/Crotonic Condensation and Related Transformations5.2 Enolization6 Functionalization of the Indole Core6.1 [4+2] Cycloaddition6.2 [3+3] Annulation6.3 Electrocyclic Reactions7 Miscellaneous8 Conclusions

Chiral phosphoric acid-catalyzed enantioselective synthesis of functionalized pyrrolinones containing a geminal diamine core via an aza-Friedel–Crafts reaction of newly developed pyrrolinone ketimines

“…The development of diverse and efficient catalytic asymmetric methods for constructing the cores of natural products has always been a hot and challenging research topic in the field of modern organic synthesis. 1 Chiral geminal diamine units are characterized by the simultaneous bonding of two nitrogen atoms to the same chiral carbon atom. Along with the rapid development of natural product chemistry and medicinal chemistry, an increasing number of natural products and bioactive molecules have been discovered to contain the chiral geminal diamine core (Fig.…”

Visible-light-mediated radical reactions of indoles withpara-quinone methides using eosin Y as an organophotoredox catalyst

“…Indole-core containing molecular scaffolds are widely found in nature, and many indole-containing natural molecules and unnatural derivatives have found numerous applications in pharmaceuticals, agriculture and also in the area of materials science. 1 Over time, indolyldiarylmethanes have also become an important class of compounds due to their contributions in pharmaceutical and medicinal chemistry (Fig. 1).…”