The present invention relates to a method for producing a substituted alkyl cycloalkanone, comprising the alkylation of a cycloalkanone with an alkene derivative in the presence of a metal oxide, where n is 2 to 20, m is 0 to 10, and R is a functional group.

The present invention provides modified cycloalkyne compounds; and method of use of such compounds in modifying biomolecules. The present invention features a cycloaddition reaction that can be carried out under physiological conditions. In general, the invention involves reacting a modified cycloalkyne with an azide moiety on a target biomolecule, generating a covalently modified biomolecule. The selectivity of the reaction and its compatibility with aqueous environments provide for its application in vivo (e.g., on the cell surface or intracellularly) and in vitro (e.g., synthesis of peptides and other polymers, production of modified (e.g., labeled) amino acids).

The present disclosure is directed to novel derivatives of naturally occurring humulones and lupulones, methods of making them, compositions comprising them, and methods for using them.

The present disclosure relates to methods of carbon-carbon bond fragmentation.

The present disclosure relates to methods of carbon-carbon bond fragmentation.

A process for the synthesis of trans-fused -lactones having Formula (IV) from substituted cyclic ketones having Formula (I). A diastereoselective synthesis of ()-epianastrephin (1) (wherein: R.sup.1 is ethenyl, R.sup.2 and R.sup.3 is methyl, and n is 1), ()-anastrephin (2) (wherein: R.sup.2 is ethenyl, R.sup.1 and R.sup.3 is methyl and n is 1), and analogs thereof (wherein: R.sup.1 is H, C.sub.1-5 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl, R.sup.2 is H, C.sub.1-5 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl, R.sup.1 and R.sup.2 together with the carbon atom they are attached form a C.sub.3-6 cycloalkyl ring, R.sup.3 is C.sub.1-5 alkyl and n is 0-2): ##STR00001##

A process for the synthesis of trans-fused -lactones having Formula (IV) from substituted cyclic ketones having Formula (I). A diastereoselective synthesis of ()-epianastrephin (1) (wherein: R.sup.1 is ethenyl, R.sup.2 and R.sup.3 is methyl, and n is 1), ()-anastrephin (2) (wherein: R.sup.2 is ethenyl, R.sup.1 and R.sup.3 is methyl and n is 1), and analogs thereof (wherein: R.sup.1 is H, C.sub.1-5 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl, R.sup.2 is H, C.sub.1-5 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl, R.sup.1 and R.sup.2 together with the carbon atom they are attached form a C.sub.3-6 cycloalkyl ring, R.sup.3 is C.sub.1-5 alkyl and n is 0-2): ##STR00001##

A process for the synthesis of trans-fused -lactones having Formula (IV) from substituted cyclic ketones having Formula (I). A diastereoselective synthesis of ()-epianastrephin (1) (wherein: R.sup.1 is ethenyl, R.sup.2 and R.sup.3 is methyl, and n is 1), ()-anastrephin (2) (wherein: R.sup.2 is ethenyl, R.sup.1 and R.sup.3 is methyl and n is 1), and analogs thereof (wherein: R.sup.1 is H, C.sub.1-5 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl, R.sup.2 is H, C.sub.1-5 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl, R.sup.1 and R.sup.2 together with the carbon atom they are attached form a C.sub.3-6 cycloalkyl ring, R.sup.3 is C.sub.1-5 alkyl and n is 0-2): ##STR00001##

The present invention relates to a method for producing a substituted alkyl cycloalkanone of formula (I), having the alkylation of a cycloalkanone of formula (II) with an alkene derivative of formula (III) in the presence of a metal oxide, where n is 2 to 20, m is 0 to 10, and R is a functional group.

The present invention relates to a method for producing a substituted alkyl cycloalkanone of formula (I), having the alkylation of a cycloalkanone of formula (II) with an alkene derivative of formula (III) in the presence of a metal oxide, where n is 2 to 20, m is 0 to 10, and R is a functional group.