John E. Thorpe

Studies concerning the antibiotic actinonin. Part V. Synthesis of structural analogues of actinonin by the anhydride–ester method

A synthetic route, associated with a high degree of stereoselectivity, has been developed for the synthesis of structural analogues (XIII) of actinonin (I). The anhydride–imide method involves the sequence (IIIb)+(V)→[(VI)+(VII)]→(XI)→(XIII). (±)-Amino-amides (IIIb) yielded the (±)-hydroxamic acids with the relative configuration (XIII) and L-amino-amides (X) yielded single enantiomers with the absolute configuration (XIII).

Studies concerning the antibiotic actinonin. Part VI. Synthesis of structural analogues of actinonin by dicyclohexylcarbodi-imide coupling reactions

The coupling of amino-amides (I) with monoalkyl esters (V) of dicarboxylic acids has been investigated as a route for the specific synthesis of structural analogues (II) and (III) of actinonin (XVII). Methods for the synthesis of the isomers (X) and (XI) have been developed, but their coupling with amino-amides (I) by use of dicyclohexylcarbodi-imide is not specific.

Total synthesis of the antibiotic, actinonin

A regioselective and stereoselective synthesis of the antibiotic, actinonin (1), is described.

Studies concerning the antibiotic actinonin. Part II. Total synthesis of actinonin and some structural analogues by the isomaleimide method

A general method for the synthesis of actinonin (I) and several structural analogues is described. L-Valyl-L-prolinol (III) and the isomaleimide (XIV) yield the intermediate (XVII), which gives actinonin (I) on hydrogenation. Corresponding routes yield compounds (XXV)(L-alanylpyrrolidine and DL-alanylpyrrolidine analogues), (XXVI)(L-valylpyrrolidine analogue), and (XXVII)(L-valyl-L-prolinol analogue), which are actinonin analogues lacking the pentyl side-chain.

Studies concerning the antibiotic actinonin. Part VII. Mass spectra of actinonin and related compounds

An interpretation of the mass spectrum of actinonin (I) is proposed on the basis of the mass spectral fragmentation patterns of the model compounds (II)–(V).

Regiospecific and stereoselective synthesis of analogues of the antibiotic, actinonin

Regiospecificity and stereoselectivity in the synthesis of actinonin structural analogues (2) and (3) are described; a stereospecific route to compounds (2) is described.