Synthesis of bicyclic compounds and method for their use as therapeutic agents

A composition, comprising:

• one or more compounds having a formula
• where V, Va, Vb, and Vc independently are selected from CR11R12, C(R11)2, CR12R13, C(R13)2, SO2, SO, S, O, NR11, CO, and Se;
• W is nitrogen, CR10, or CR11;
• R10 is H, alkyl or (CH2)nOH;
• R11 is H, alkyl, branched alkyl, cyclic alkyl, aryl, heteroaryl, and any combination thereof;
• R12 is H, (CH2)nZH, (CH2)nZR11, (CH2)nZ(CO)R11, (CH2)nZ(SO2)R11, (CH2)nZ(CO)NH2, (CH2)nZ(CO)OR11, or (CH2)nZ(CNH)NH2, and Z═O, S, Se, or NR11;
• R13 is H, alkyl, branched alkyl, cyclic alkyl, alkenyl, alkynyl, aryl, a heteroatom-containing moiety, and any combination thereof;
• if Va comprises CR11R12, C(R11)2, CR12R13, or C(R13)2, then Va and Vb together can comprise a lactone or a lactam;
• if Vc comprises CR11R12, C(R11)2, CR12R13, or C(R13)2 and has at least two substituents selected from R11, R12, or R13, or any combination thereof, then the two substituents together can form a cyclic alkyl group;
• n=0, 1 or 2;
• m=0, 1 or 2;
• and
• at least one biologically acceptable material.

A conjugate, comprising:

• a compound having a formula
• where V, Va, Vb, and Vc independently are selected from CR11R12, C(R11)2, CR12R13, C(R13)2, SO2, SO, S, O, NR11, CO, and Se;
• W is nitrogen, CR10, or CR11;
• R10 is H, alkyl or (CH2)OH;
• R11 is H, alkyl, branched alkyl, cyclic alkyl, aryl, a heteroatom-containing moiety, and any combination thereof;
• R12 is H, (CH2)nZH, (CH2)nZR11, (CH2)nZ(CO)R11, (CH2)nZ(SO2)R11, (CH2)nZ(CO)NH2, (CH2)nZ(CO)OR11, or (CH2)nZ(CNH)NH2, and Z═O, S, Se, or NR11;
• R13 is H, alkyl, branched alkyl, cyclic alkyl, alkenyl, alkynyl, aryl, a heteroatom-containing moiety, and any combination thereof;
• if Va comprises CR11R12, C(R11)2, CR12R13, or C(R13)2, then Va and Vb together can comprise a lactone or a lactam;
• if Vc comprises CR11R12, C(R11)2, CR12R13, or C(R13)2 and has at least two substituents selected from R11, R12, or R13, or any combination thereof, then the two substituents together can form a cyclic alkyl group;
• n=0, 1 or 2;
• m=0, 1 or 2;
• and
• a specific binding moiety, a signal generating moiety, and combinations thereof.

A method for making a bicyclic compound, comprising:

• oxidizing cyclooctadiene with peracetic acid to make an oxidized cyclooctadiene;
• treating the oxidized cyclooctadiene with a base to form a bicyclic intermediate having a structure
• and
• oxidizing the bicyclic intermediate with selenium dioxide or CO3-pyridine.