Litcius/Paper detail

Recent Advances in Stereoselective Ring Expansion of Spirocyclopropanes: Access to the Spirocyclic Compounds

Tanumay Sarkar, Bijay Ketan Das, Kangkan Talukdar, Tariq A. Shah, Tharmalingam Punniyamurthy

2020ACS Omega55 citationsDOIOpen Access PDF

Abstract

Spirocyclopropane represents a privileged structural scaffold for accessing synthetic libraries of densely functionalized spirocarbo- and heterocyclic compounds. Due to the ubiquity of spirocyclic motifs as a potent pharmacophore in natural products and pharmaceuticals, recent years have witnessed significant advances in developing synthetic strategies that exploits carbon-carbon bond scission in spirocyclopropanes. This paper summarizes the recent developments in stereoselective ring expansion of spirocyclopropanes in diversity-oriented synthesis and highlights the synthetic as well as mechanistic rationale of those methodologies. This review also encompasses the applicability of the protocols in bioactive natural product syntheses.

Topics & Concepts

PharmacophoreStereoselectivityNatural productRing (chemistry)Combinatorial chemistryChemistryStereochemistryOrganic chemistryCatalysisCyclopropane Reaction MechanismsAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry Methods