Synthesis of the organoarsenical antibiotic arsinothricin and derivatives thereof

A derivative of arsinothricin (AST) having a general structure of formula

• wherein X is O or S;
• Z is OR7, NHR8, NR8R9 or NHCHR20R11;
• R1 and R2 are independently selected from hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, cycloalkyl, substituted cycloalkyl, acyl, benzyl, and benzoyl;
• R3 is hydrogen, alky, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkoxy or hydroxylalkyl;
• R4 is OH, OR14, alkyl, substituted alkyl, aryl, substituted aryl, heteroalkyl, substituted heteroalkyl, cycloalkyl, substituted cycloalkyl, acyl, benzyl, benzoyl or sulfhydryl;
• R5 is alkyl, substituted alkyl, aryl, substituted aryl, heteroalkyl, substituted heteroalkyl, cycloalkyl, substituted cycloalkyl, acyl, benzyl, benzoyl or sulfhydryl;
• R6 is hydrogen, halogen, alkyl, substituted alkyl, acyl, alkoxy, cycloalkyl, substituted cycloalkyl, amino, substituted amino, or hydroxyl;
• R7 is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, benzyl, benzoyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, or substituted heteroalkyl;
• R8 is hydrogen, alkyl, substituted alkyl, substituted alkyl, aryl, substituted aryl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, acyl, alkoxy, benzyl, and benzoyl;
• R9 is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, acyl, alkoxy, benzyl, or benzoyl;
• R10 is hydrogen, alkyl, substituted alkyl, substituted alkyl, aryl, substituted aryl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, acyl, alkoxy, amino, or substituted amino, benzyl, and benzoyl;
• R11 is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, cycloalkyl, substituted cycloalkyl, heteroalkyl, substituted heteroalkyl, acyl, alkoxy, benzyl, benzoyl amino, or substituted amino;
• and
• R14 is alkyl, substituted alkyl, aryl, or substituted aryl,
• or a salt thereof.