Methods of making indole analogs using a rhodium-containing catalyst are described, along with methods of using the compounds to treat hyperglycemic, hyperlipidemic, or autoimmune disorders in mammals, and corresponding pharmaceutical compositions. Disclosed herein is a method of making indoles. The method comprises contacting a reactant of formula I wherein E is a protecting group, —SO2-Aryl, or —SO2-substituted-Aryl; and R and R2 are independently selected from the group consisting of hydrogen, halo, C1-C12-alkyl and aryl; with a rhodium(l)-containing catalyst.

Methods of making indole analogs using a rhodium-containing catalyst are described, along with methods of using the compounds to treat hyperglycemic, hyperlipidemic, or autoimmune disorders in mammals, and corresponding pharmaceutical compositions. Disclosed herein is a method of making indoles. The method comprises contacting a reactant of formula I wherein E is a protecting group, —SO2-Aryl, or —SO2-substituted-Aryl; and R and R2 are independently selected from the group consisting of hydrogen, halo, C1-C12-alkyl and aryl; with a rhodium(l)-containing catalyst.

Provided is an alkyldiphenylmethane protective agent, which can prevent solidification or insolubilization of a compound by protecting a functional group of the compound to achieve easy separation and purification after a reaction. An alkyldiphenylmethane compound represented by general formula (1): ##STR00001## wherein Y represents —OR.sup.19 (wherein R.sup.19 represents a hydrogen atom or an active ester-type protecting group), —NHR.sup.20 (wherein R.sup.20 represents a hydrogen atom, a C.sub.1-6 linear or branched alkyl group, or an aralkyl group), isocyanate group, an azide group, or a halogen atom, Z represents a C.sub.1-4 linear or branched alkyl group, an alkenyl group, or a cycloalkyl group, at least one of R.sup.1 to R.sup.10 represents a group represented by formula (2):
—O—R.sup.11—X-A  (2) and the others each independently represent a hydrogen atom, a halogen atom, a C.sub.1-4 alkyl group, or a C.sub.1-4 alkoxy group; R.sup.11 represents a C.sub.1-16 linear or branched alkylene group; X represents O or CONR.sup.21 (wherein R.sup.21 represents a hydrogen atom or a C.sub.1-4 alkyl group); and A represents, for example, a group represented by formula (3): ##STR00002## wherein R.sup.12, R.sup.13, and R.sup.14 may be the same or different and each independently represent a C.sub.1-6 linear or branched alkyl group or an optionally substituted aryl group; R.sup.15 represents a single bond or a C.sub.1-3 linear or branched alkylene group; and R.sup.16, R.sup.17, and R.sup.18 each independently represent a C.sub.1-3 linear or branched alkylene group.

Disclosed herein is a method of forming a compound of formula I: ##STR00001##
wherein the substituents are defined in the specification. In particular, the compounds of formula I can be converted to amino acids bearing quaternary stereocenters with exceptional optical purities.

Disclosed herein is a method of forming a compound of formula I: ##STR00001##
wherein the substituents are defined in the specification. In particular, the compounds of formula I can be converted to amino acids bearing quaternary stereocenters with exceptional optical purities.

The purpose of the present invention is to provide a protecting group which improves the solubility of a compound having a functional group protected with the protecting group in an organic solvent and which is easily separated and purified after a reaction with avoiding solidification or insolubilization. Provided is a benzyl compound represented by Formula (1) where X.sup.1 represents —CH.sub.2OR.sup.14 (where R.sup.14 represents a hydrogen atom, a halogenocarbonyl group, or an active ester-type protecting group), —CH.sub.2NHR.sup.5 (where R.sup.15 represents a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, or an aralkyl group), a halogenomethyl group, a methyl azide group, a formyl group, or an oxime; and at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 is a group represented by Formula (2), and the remainders each represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, where R.sup.6 represents a linear or branched alkylene group having 1 to 16 carbon atoms; X.sup.2 represents O or CONR.sup.16 (where R.sup.16 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms); and A represents a group represented by Formula (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), or (13).

The purpose of the present invention is to provide a protecting group which improves the solubility of a compound having a functional group protected with the protecting group in an organic solvent and which is easily separated and purified after a reaction with avoiding solidification or insolubilization. Provided is a benzyl compound represented by Formula (1) where X.sup.1 represents —CH.sub.2OR.sup.14 (where R.sup.14 represents a hydrogen atom, a halogenocarbonyl group, or an active ester-type protecting group), —CH.sub.2NHR.sup.5 (where R.sup.15 represents a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, or an aralkyl group), a halogenomethyl group, a methyl azide group, a formyl group, or an oxime; and at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 is a group represented by Formula (2), and the remainders each represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, where R.sup.6 represents a linear or branched alkylene group having 1 to 16 carbon atoms; X.sup.2 represents O or CONR.sup.16 (where R.sup.16 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms); and A represents a group represented by Formula (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), or (13).

The present disclosure relates to novel, scalable methods of making substituted tricyclic compounds that are useful to treat and/or prevent HBV and/or HBV-HDV infection and related conditions in a subject.

An object of the present invention is to develop a protecting group, which can prevent solidification or insolubilization of a compound by protecting a functional group to achieve easy separation and purification after a reaction. A diphenylmethane compound represented by general formula (1): ##STR00001## wherein Y represents —OR.sup.19 (wherein R.sup.19 represents a hydrogen atom or an active ester-type protecting group), —NHR.sup.20 (wherein R.sup.20 represents, for example, a hydrogen atom, a C.sub.1-6 linear or branched alkyl group, or an aralkyl group, at least one of R.sup.1 to R.sup.10 represents a group represented by formula (2):
—O—R.sup.11—X-A  (2) and the others each independently represent a hydrogen atom, a halogen atom, a C.sub.1-4 alkyl group, or a C.sub.1-4 alkoxy group; R.sup.11 represents a C.sub.1-16 linear or branched alkylene group; X represents O or CONR.sup.21 (wherein R.sup.21 represents a hydrogen atom, or a C.sub.1-4 alkyl group; and A represents, for example, a group represented by formula (3). ##STR00002##

An object of the present invention is to develop a protecting group, which can prevent solidification or insolubilization of a compound by protecting a functional group to achieve easy separation and purification after a reaction. A diphenylmethane compound represented by general formula (1): ##STR00001## wherein Y represents —OR.sup.19 (wherein R.sup.19 represents a hydrogen atom or an active ester-type protecting group), —NHR.sup.20 (wherein R.sup.20 represents, for example, a hydrogen atom, a C.sub.1-6 linear or branched alkyl group, or an aralkyl group, at least one of R.sup.1 to R.sup.10 represents a group represented by formula (2):
—O—R.sup.11—X-A  (2) and the others each independently represent a hydrogen atom, a halogen atom, a C.sub.1-4 alkyl group, or a C.sub.1-4 alkoxy group; R.sup.11 represents a C.sub.1-16 linear or branched alkylene group; X represents O or CONR.sup.21 (wherein R.sup.21 represents a hydrogen atom, or a C.sub.1-4 alkyl group; and A represents, for example, a group represented by formula (3). ##STR00002##