Studies toward a synthesis of C3-epimauritine D: construction of the macrocycle

Macrocyclization strategies for cyclic peptides and peptidomimetics

“…161 To date, however, ether-containing cyclic peptides are predominantly accessed by other cyclization reactions, with the ether moiety introduced as part of a pre-formed building block. 144,[162][163][164][165]…”

Amino acid fluorides: viable tools for synthesis of peptides, peptidomimetics and enantiopure heterocycles

“…The use of acid uorides in macrocyclisation has been illustrated in the preparation of cyclosporine A derivatives 137 which exhibited non-immunosuppressive and anti-HIV activity and in the synthesis of a 14 membered cyclic enamide of C3epimauritine D. 138 Three macrocyclic dilactones have also been made using Cbz-glutamyl diuoride as well as Cbz-cystyl diuoride. 87 5.2.1 Cyclosporine A derivatives.…”

“…5.2.2 Cyclic enamide of C3-epimauritine D. Kim et al reported the synthesis of a key intermediate cyclic enamide of C3-epimauritine D by macrocyclisation at the C1-N14 site using TFFH in the presence of HOAt. 138 Cyclization of the intermediate (121), was attempted (aer removal of the Cbz group) using activated pentauorophenyl (Pfp) ester, but the method failed. Other reagents including BOP-Cl, diphenylphosphoryl azide and BOP did not give the expected product either.…”

A new convenient way to synthesize 1‐hydroxyphosphonates from heterocyclic aldehydes and ketones under microwave irradiation

“…Although there are many attractive routes for the synthesis of 1-hydroxyphosphonates [21][22][23][24][25][26][27][28][29][30][31], the aldehyde substrates are often limited to alkyl and aryl aldehydes. On the other hand, many heterocyclic phosphonates have been proven to be biologically active [32][33][34].…”