Methods of synthesis and uses of agrimol compounds

A compound having the structure of

• wherein:
• (a) L1 and L2 are independently a single bond or a substituted or unsubstituted alkylene;
• (b) R1—R3 are hydroxyl;
• (c) -L3-A3 is a substituted or unsubstituted alkyl, or
• R17 is a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, or
• m is an integer from 0 to 5 and R26 is a carboxylic acid, an ester, an amino, or an amide;
• (d) L4 and L5 are independently a single bond, a substituted or unsubstituted alkylene, or a carbonyl;
• (e) A4 and A5 are independently a hydrogen, a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, a carbonyl, or an alkoxy;
• (f) R9—R16 are independently a hydrogen, a hydroxyl, a substituted or unsubstituted alkyl, a carbonyl, or an alkoxy;
• and
• (g) the substituents, when present, are independently a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted heterocyclyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted polyheteroaryl, a substituted or unsubstituted aralkyl, a carbonyl, an alkoxy, a halogen, a hydroxyl, a phenoxy, a thiol, an alkylthio, a phenylthio, an arylthio, a cyano, an isocyano, a nitro, an carboxyl, an amino, an amido, an oxo, a silyl, a sulfinyl, a sulfonyl, a sulfonic acid, a phosphonium, a phosphanyl, a phosphoryl, or a phosphonyl,
• with the proviso that:
• (i) when -L3-A3, -L4-A4, and -L5-A5 are
• and R17 is an unsubstituted C1-C4 alkyl, then -L3-A3 is not —C(O)-(n-propyl) and not —C(O)-(isobutyl);
• and
• (ii) when -L3-A3, -L5-A5, and R10 are
• and R17 is an unsubstituted C1-C3 alkyl, then -L3-A3 is not —C(O)-(n-propyl) and not —C(O)-(isopropyl).

A compound having the structure of

• wherein:
• (a) L2 is a single bond or an unsubstituted alkylene;
• (b) L1 is —C(O)—, and A1 is a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, or an alkoxy;
• (c) R1—R3 are a hydroxyl;
• (d) R1—R16 are independently a hydrogen, a hydroxyl, a substituted or unsubstituted alkyl, a carbonyl, —OR4, —SR5, or —NR6R7, R4—R7 are independently a hydrogen or a substituted or unsubstituted alkyl;
• (e) -L3-A3 is
• R17 is a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl;
• (f) -L5-A5 is a hydrogen, a substituted or unsubstituted alkyl, or
• R17 is a substituted or unsubstituted alkyl;
• and
• (g) the substituents, when present, are independently a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted heterocyclyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted polyheteroaryl, a substituted or unsubstituted aralkyl, a carbonyl, an alkoxy, a halogen, a hydroxyl, a phenoxy, a thiol, an alkylthio, a phenylthio, an arylthio, a cyano, an isocyano, a nitro, an carboxyl, an amino, an amido, an oxo, a silyl, a sulfinyl, a sulfonyl, a sulfonic acid, a phosphonium, a phosphanyl, a phosphoryl, or a phosphonyl,
• with the proviso that:
• (i) when -L1-A1 and -L3-A3 are the same
• then R17 is not methyl.

A method for synthesizing a compound of Formula I,

• the method comprising:
• (i) heating a reaction mixture at a suitable temperature for a period of time sufficient to form a product comprising the compound, wherein the reaction mixture comprises a solvent, a first reactant having the structure of Formula V,
• a second reactant having the structure of Formula VI, and
• a third reactant having the structure of Formula VII,
• wherein
• (a) L1 and L2 are independently a bond (single, double, or triple), a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a carbonyl, or an alkoxy;
• (b) L3 is a bond (single, double, or triple), a substituted or unsubstituted alkyl, or a carbonyl;
• (c) A1 and A2 are independently a hydrogen, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted aryl, a carbonyl, or an alkoxy, and at least one of A1 and A2 is a substituted or unsubstituted aryl;
• (d) A3 is a hydrogen, a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, a carbonyl, or an alkoxy;
• (e) R1—R3 are independently a hydrogen, a hydroxyl, a substituted or unsubstituted alkyl, a carbonyl, an alkoxy, a thiol, or an amino;
• (f) R23—R25 are independently a hydrogen or a substituted or unsubstituted alkyl;
• and
• (g) the substituents are independently a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted heterocyclyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted polyheteroaryl, a substituted or unsubstituted aralkyl, a carbonyl, an alkoxy, a halogen, a hydroxyl, a phenoxy, a thiol, an alkylthio, a phenylthio, an arylthio, a cyano, an isocyano, a nitro, an carboxyl, an amino, an amido, an oxo, a silyl, a sulfinyl, a sulfonyl, a sulfonic acid, a phosphonium, a phosphanyl, a phosphoryl, or a phosphonyl, and
• wherein the second reactant is the same as or different from the third reactant.