The present invention discloses a cyclopenta[c]chromene compound and a preparation method thereof. A chalcone compound as a reactant, A cationic rare earth metal compound Ln(CH.sub.3CN).sub.9].sup.3+[(AlCl.sub.4).sub.3].sup.3−.CH.sub.3CN as a catalyst, and 2-naphthalenethiol as an accelerator, react in an organic solvent to prepare the cyclopenta[c]-chromene compound. Ln represents a positive trivalent rare earth metal ion, which is selected from the group consisting of La, Nd, Sm, Gd, and Yb. The starting materials are easy obtained, the reaction process is simple, and the yield of the target product is high, up to 85%.

Disclosed are a series of compounds or their tautomers having a general structure represented by Formula Ia, Ib, IIa, IIb, or IIc and pharmaceutically acceptable salts thereof. The present disclosure also relates to pharmaceutical compositions comprising said compounds or tautomers. The present disclosure further relates to a method of treating a disease or condition associated with iron dysregulation or dysfunctional iron homeostasis comprising administering to a subject in need thereof a therapeutically effective amount of Formula Ia, Ib, IIa, IIb, or IIc compounds or tautomers.

Disclosed are a series of compounds or their tautomers having a general structure represented by Formula Ia, Ib, IIa, IIb, or IIc and pharmaceutically acceptable salts thereof. The present disclosure also relates to pharmaceutical compositions comprising said compounds or tautomers. The present disclosure further relates to a method of treating a disease or condition associated with iron dysregulation or dysfunctional iron homeostasis comprising administering to a subject in need thereof a therapeutically effective amount of Formula Ia, Ib, IIa, IIb, or IIc compounds or tautomers.

The invention relates to enzymes and methods for producing a monoterpenoid compound. In one aspect, the invention is a method for producing a monoterpenoid compound, comprising the steps of (1) providing a monoterpenoid precursor; (2) providing a NEPS enzyme; and (3) contacting the monoterpenoid precursor with the enzyme under catalytic conditions to produce an monoterpenoid compound.

The present disclosure provides isolated nepetalactone oxidoreductase polypeptides (NORs), nepetalactol synthases (NEPSs), and related polynucleotides, engineered host cells, and cultures, as well as methods for producing NORs and NEPSs, and for using them to produce nepetalactol, nepetalactone, and dihydronepetalactone. The present disclosure also provides methods for engineering cells (e.g., microbial cells) to produce nepetalactone from a fermentation substrate such as glucose, as well as engineered cells having this capability and related cultures and methods for producing nepetalactone.

Method for decarboxylating a carboxylated phytocannabinoid compound of Formula I to form a phytocannabinoid compound of Formula II: Formula I Formula II wherein: R1 is selected from the group consisting of: substituted or unsubstituted C.sub.1-C.sub.5 alkyl; R2 is selected from the group consisting of: OH or O, and R3 is selected from the group consisting of: a substituted or unsubstituted cyclohexene, a substituted or unsubstituted C.sub.2-C.sub.8 alkene, or a substituted or unsubstituted C.sub.2-C.sub.8 dialkene; or R2 is O, and R2 and R3 together form a ring structure in which R2 is an internal ring atom; wherein the method includes heating a reaction mixture comprising the carboxylated phytocannabinoid compound and a polar aprotic solvent in the presence of a LiCl for a time sufficient to decarboxylate at least a portion of the carboxylated phytocannabinoid compounds and form the phytocannabinoid compound. ##STR00001##

Method for decarboxylating a carboxylated phytocannabinoid compound of Formula I to form a phytocannabinoid compound of Formula II: Formula I Formula II wherein: R1 is selected from the group consisting of: substituted or unsubstituted C.sub.1-C.sub.5 alkyl; R2 is selected from the group consisting of: OH or O, and R3 is selected from the group consisting of: a substituted or unsubstituted cyclohexene, a substituted or unsubstituted C.sub.2-C.sub.8 alkene, or a substituted or unsubstituted C.sub.2-C.sub.8 dialkene; or R2 is O, and R2 and R3 together form a ring structure in which R2 is an internal ring atom; wherein the method includes heating a reaction mixture comprising the carboxylated phytocannabinoid compound and a polar aprotic solvent in the presence of a LiCl for a time sufficient to decarboxylate at least a portion of the carboxylated phytocannabinoid compounds and form the phytocannabinoid compound. ##STR00001##

The invention provides a novel, general, and facile strategy for the creation of small molecules with high structural and stereochemical complexity. Aspects of the methods include ring system distortion reactions that are systematically applied to rapidly convert readily available natural products to structurally complex compounds with diverse molecular architectures. Through evaluation of chemical properties including fraction of sp.sup.3 carbons, ClogP, and the number of stereogenic centers, these compounds are shown to be significantly more complex and diverse than those in standard screening collections. This approach is demonstrated with natural products (gibberellic acid, adrenosterone, and quinine) from three different structural classes, and methods are described for the application of this strategy to any suitable natural product.

The invention provides a novel, general, and facile strategy for the creation of small molecules with high structural and stereochemical complexity. Aspects of the methods include ring system distortion reactions that are systematically applied to rapidly convert readily available natural products to structurally complex compounds with diverse molecular architectures. Through evaluation of chemical properties including fraction of sp.sup.3 carbons, ClogP, and the number of stereogenic centers, these compounds are shown to be significantly more complex and diverse than those in standard screening collections. This approach is demonstrated with natural products (gibberellic acid, adrenosterone, and quinine) from three different structural classes, and methods are described for the application of this strategy to any suitable natural product.

Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).