Bile acid derivatives and methods for synthesis and use

A method of synthesizing a compound having the following structure,

• the method comprising,
• (i) contacting a compound of formula (II)
• wherein R11 is R11A or R11B, with an oxidizing reagent to provide a compound of formula (III-A) or (III-B),
• or
• (ii) when the product of step (i) has a structure according to formula (III-A), contacting the compound of formula (III-A) with an alcohol protecting agent to provide a compound of formula (III-B);
• (iii) contacting a compound of formula (III-B) with an alkylating agent in the presence of a sterically hindered base to provide a compound of formula (IV),
• (iv) optionally contacting the compound of formula (IV) with an alcohol deprotecting agent to provide a compound of formula (IV-A),
• (v) treatment of the compound of formula (IV) or (IV-A) with a reducing agent to provide a compound of formula (I) or (I-A),
• or
• and
• (vi) when the product of step (v) has a structure according to formula (I-A), contacting the compound of formula with an alcohol deprotecting agent to provide a compound of formula (I-A);
• wherein,
• L1 is —C(O)—, —C(O)O—, —C(O)NH—, or —CH2—;
• R1 is hydrogen, halogen, —N3, —CF3, —CCl3, —CBr3, —CI3, —CN, —CHO, —OR1A, —NHR1A, —COOH, —CONH2, —NO2, —SH, —SO2Cl, —SO3H, —SO4H, —SO2NH2, —NHNH2, —ONH2, —NHC(O)NHNH2, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or a carboxylate protecting group;
• R2 is hydrogen or unsubstituted alkyl;
• R3 is hydrogen, unsubstituted alkyl, or —OR3A;
• R4 is hydrogen, unsubstituted alkyl, or —OR4A;
• R5 is hydrogen, unsubstituted alkyl, or —OR5A;
• R6 is hydrogen, unsubstituted alkyl, or —OR6A;
• R7 is hydrogen, unsubstituted alkyl, or —OR7A;
• R8 is hydrogen, unsubstituted alkyl, or —OR8A;
• R9 is hydrogen, unsubstituted alkyl, or —OR9A;
• R10 is hydrogen, unsubstituted alkyl, or —OR10A;
• R11A is hydrogen;
• R11B is an alcohol protecting group;
• R12 is hydrogen, unsubstituted alkyl, or —OR12A;
• R13 is unsubstituted alkyl;
• R1A, R3A, R4A, R5A, R6A, R7A, R8A, R9A, R10A, R12A and R13A are independently hydrogen, unsubstituted alkyl, or an alcohol protecting group.