Cover Feature: Synthesis of Pyrrolo[2,1‐a]isoquinoline Class of Natural Product Crispine A (Eur. J. Org. Chem. 35/2021)

Abstract

The Cover Feature shows naturally occurring (2S,3S)‐ and (2S,3R)‐tetrahydro‐3‐hydroxy‐5‐oxo‐2,3‐furan dicarboxylic acid bearing, chemically amenable functional groups that are an ideal choice for the enantiopure synthesis of the (−)‐ and (+)‐Crispine A, respectively. The diastereomeric natural products are conveniently converted to desirable enantiomers of Crispine A through the chiral pool strategy. This exciting and efficient strategy is one of the well‐explored trends in synthetic organic chemistry, especially regarding molecules procured from tropical plant material (Nature) and serves as key step in the enantiopure synthesis of small‐molecule natural products. More information can be found in the Minireview by C. Mohan, I. Ibnusaud et al.

Diversely functionalized isoquinolines and their core-embedded heterocyclic frameworks: a privileged scaffold for medicinal chemistry

“…45,86 Apart from this, the core constitutes and embellishes the structure of numerous chiral alkaloids. 27,28…”

“…There is a profound increase in research reports published yearly on the synthetic accomplishments in constructing the complex structures of the isoquinoline skeleton in non-racemic and enantiopure forms. 27–31 The studies on isoquinoline scaffolds offer new opportunities in medicinal and bioorganic chemistry due to their therapeutic applications. 32–35 Novel synthetic methodologies are reported in constructing isoquinoline skeletons instead revolving around the traditional Pictet–Spengler, Bischler–Napieralski, Pomeranz–Fritsch, and Bobbitt reaction procedures.…”