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.

A process for the synthesis of trans-fused γ-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 γ-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 γ-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 disclosure relates to methods of carbon-carbon bond fragmentation.

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

Chiral polyvinylpyrrolidinone (CSPVP), complexes of CSPVP with a core species, such as a metallic nanocluster catalyst, and enantioselective oxidation reactions utilizing such complexes are disclosed. The CSPVP complexes can be used in asymmetric oxidation of diols, enantioselective oxidation of alkenes, and carbon-carbon bond forming reactions, for example. The CSPVP can also be complexed with biomolecules such as proteins, DNA, and RNA, and used as nanocarriers for siRNA or dsRNA delivery.

Chiral polyvinylpyrrolidinone (CSPVP), complexes of CSPVP with a core species, such as a metallic nanocluster catalyst, and enantioselective oxidation reactions utilizing such complexes are disclosed. The CSPVP complexes can be used in asymmetric oxidation of diols, enantioselective oxidation of alkenes, and carbon-carbon bond forming reactions, for example. The CSPVP can also be complexed with biomolecules such as proteins, DNA, and RNA, and used as nanocarriers for siRNA or dsRNA delivery.

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 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.