New Construction of Biologically Active Substances using Diphenyl Phosphorazidate

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Diphenyl phosphorazidate (DPPA, <(C_6H_5O)_2> P(O) <N_3> ) is a versatile synthetic reagent. DPPA can be used for (1) the peptide bond formation (N-acylation), (2) the carbon-carbon bond formation (C-acylation), and (3) the introduction of amino functions (amination). By use of these DPPA-mediated reactions as key steps, new construction of biologically active substances has been developed. Several antineoplastic and/or cytotoxic cyclic peptides of marine origin such as dolastatin 3, ascidiacyclamide, patellamides A, B, C, ulithiacyclamide, and ulicyclamide have been prepared using the reaction (1). The C-acylation (2) has been applied to efficient syntheses of L-daunosamine, L-vancosamine, D-ristosamine, and mugineic acid. Tilivalline has been also synthesized through the amination (3) using DPPA.