Design, Synthesis and Late‐Stage Modification of Indane‐Based Peptides via [2+2+2] Cyclotrimerization. Issue 22 (22nd September 2021)

• Record Type: Journal Article
• Authors: Kotha, Sambasivarao; Kumar Gupta, Naveen; Sreevani, Gaddamedi; Rao Panguluri, Nageswara
• Is Part Of: Chemistry, an Asian journal. Volume 16:Issue 22(2021)
• Page Start: 3649
• Page End: 3657
• Publication Date: 2021-09-22
• Subjects: Indane-based dipepeptide -- [2+2+2] cyclotrimerization -- Sonogashira Coupling -- Diels–Alder reaction -- Suzuki Coupling; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.202100825
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: Here, we prepared several dipeptides containing 2‐aminoindane‐2‐carboxylic acid (Aic) and carried out further synthetic transformations. Synthesis and purification of modified peptides by using [2+2+2] cyclotrimerization is a challenging task. We are able to modify the unusual amino acids and peptide derivatives by late‐stage incorporation of benzylhalo functionality. To incorporate benzylhalo moiety we used [2+2+2] cyclotrimerization in the presence of Mo(CO)6 . These halo derivatives are potential substrates for further modification by Sonogashira reaction, Suzuki–Miyaura cross‐coupling, sultine formation, and the Diels–Alder reaction sequence. Abstract : Indane‐based peptides are biologically important compounds . Here, we carried out late stage modification of dipeptides containing 2‐aminoindan‐2‐carboxylic acid (Aic) via Sonogashira coupling, [2+2+2] cyclotrimerization, sultine formation, Diels–Alder reaction and Suzuki–Miyaura cross coupling as key steps.