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(1)-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(1)-containing catalyst.

A novel agent for introducing a protecting group for a hydroxy group and/or a mercapto group that can be introduced and removed under mild conditions is provided. The agent for introducing a protecting group for a hydroxy group and/or mercapto group of a substrate compound having the hydroxy group and/or mercapto group is represented by the following formula (I), wherein A represents a ring structure having 1 to 5 rings in which two carbon atoms of an adjacent benzene ring are included, the ring structure comprises a substituted or unsubstituted five-membered ring or six-membered ring and optionally include a heterocycle; each of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 is independently a hydrogen atom or a linear or branched alkyl group having 1 to 5 carbon atoms; and X is a halogen atom or OSO.sub.2R.sup.5 (R.sup.5=an aryl group or an alkyl group).

A novel agent for introducing a protecting group for a hydroxy group and/or a mercapto group that can be introduced and removed under mild conditions is provided. The agent for introducing a protecting group for a hydroxy group and/or mercapto group of a substrate compound having the hydroxy group and/or mercapto group is represented by the following formula (I), wherein A represents a ring structure having 1 to 5 rings in which two carbon atoms of an adjacent benzene ring are included, the ring structure comprises a substituted or unsubstituted five-membered ring or six-membered ring and optionally include a heterocycle; each of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 is independently a hydrogen atom or a linear or branched alkyl group having 1 to 5 carbon atoms; and X is a halogen atom or OSO.sub.2R.sup.5 (R.sup.5=an aryl group or an alkyl group).

A process for making ixazomib citrate of formula VI comprising reacting a compound of formula V with citric acid to form ixazomib citrate of formula VI: ##STR00001## wherein R is hydrogen or an amide protecting group.

A process for making ixazomib citrate of formula VI comprising reacting a compound of formula V with citric acid to form ixazomib citrate of formula VI: ##STR00001## wherein R is hydrogen or an amide protecting group.

An object of the present invention is to provide a novel tetrahydroazepine compound and a process for producing the same.

The present invention relates to a tetrahydroazepine compound represented by the formula (10) or a salt thereof, and

a process for producing the said compound or a salt thereof.

##STR00001## (In the formula, R.sup.1 is an optionally substituted alkyl group, R.sup.2 is an optionally substituted alkyl group and one of the XY bond and the YZ bond is a carbon-carbon double bond and the other is a carbon-carbon single bond.)

The present invention provides a method for producing a benzaldehyde in which an amino group is bonded in the 2 position, a halogeno group or an alkoxy group is bonded in the 3 position, and a hydrogen atom, an alkyl group, a halogeno group, an alkoxy group, or a cyano group is bonded independently in each of the 4, 5, and 6 positions, the method including: preparing a benzaldehyde in which a halogeno group or an alkoxy group is bonded in the 3 position, a hydrogen atom is bonded in the 2 position, and a hydrogen atom, an alkyl group, a halogeno group, an alkoxy group, or a cyano group is bonded independently in each of the 4, 5, and 6 positions so that a lithiation reaction is most active at the 2 position; acetal-protecting a formyl group in the benzaldehyde; sequentially performing lithiation, azidation, and amination of the 2 position; and the performing acetal deportection.

The present invention relates to a method for the synthesis of cyclic depsipeptides, in particular emodepside, from the open form.

Benzotriazole phenols with substituents either ortho to the phenol hydroxyl group and/or para to the phenol hydroxyl group can be prepared from the unsubstituted benzotriazole phenol by coupling reactions. The ortho substituent group can be a simple alkoxy or amino group, or the ortho substituent group can be a linking group, linking the benzotriazole phenol to another benzotriazole phenol group.