One‐Pot Preparation of Functionalized Azabicyclo[6.3.0]alkanone Amino Acids by Tandem Cross Enyne Metathesis/Ring‐Closing Metathesis. Issue 24 (8th June 2020)

• Record Type: Journal Article
• Authors: Bernardi, Eric; Colombo, Lino; De Lorenzi, Ersilia; Carraro, Massimo; Serra, Massimo
• Is Part Of: European journal of organic chemistry. Issue 24(2020)
• Page Start: 3568
• Page End: 3575
• Publication Date: 2020-06-08
• Subjects: Tandem metathesis -- One‐pot -- Azabicycloalkanone -- Amino acids -- Ruthenium -- Heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000231
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Here we report an efficient one‐pot procedure for the preparation of functionalized azabicyclo[6.3.0]alkanone amino acid derivatives. The synthetic protocol exploits an ethylene‐mediated cross enyne metathesis followed by a ring closing metathesis. The reactivity of the newly synthesized 8, 5‐fused bicyclic scaffolds has then been investigated to obtain variously functionalized derivatives with potential applications in the field of peptides/peptidomimetics. Abstract : Azabicyclo[X.Y.0]alkanone amino acids are one of the most attractive classes of rigid dipeptide surrogates employed to study conformation‐activity relationships of biologically active peptides. Here we report an efficient one‐pot synthetic approach for the preparation of 8, 5‐fused azabicycloalkane derivatives. These scaffolds, characterized by the presence of a conjugate diene system, could be exploited to design compounds with improved activity.