57440-68-3

Upstream product

• 1193-55-1 2-methylcyclohexane-1,3-dione 
• 1629-58-9 4-penten-3-one 
• 32830-97-0 1-chloro-3-pentanone 
• 32774-63-3 3-hydroxy-2-methyl-cyclohex-2-enone 

Downstream Products

• 41019-71-0 (+/-)-3,4,8,8a-tetrahydro-5,8a-dimethyl-1,6(2H,7H)-naphthalenedione 
• 113666-06-1 (-)-(4aR)-1,4a-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione 
• 41722-49-0 (S)-1,4a-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione 
• 615556-87-1 (1S,6S)-3-ethyl-3-hydroxy-6-methyl-2-oxabicyclo[4.4.0]decan-7-one 

Relevant academic research and scientific papers

Heterogeneous amine catalyst grafted on amorphous silica: An effective organocatalyst for microwave-promoted Michael reaction of 1,3-dicarbonyl compounds in water

Michael addition of a 1,3-dicarbonyl compound to an α,β- unsaturated carbonyl compound was effectively catalyzed by heterogeneous N,N-diethylaminopropylated silica gel (NDEAP) in water under microwave heating. The reaction condition was mild, practical, a

Synthesis of the seco-Limonoid BCD Ring System Identifies a Hsp90 Chaperon Machinery (p23) Inhibitor

D-Ring-seco-limonoids (tetranortriterpenoids), such as gedunin and xylogranin B display anti-cancer activity, acting via inhibition of Hsp90 and/or associated chaperon machinery (e.g., p23). Despite this, these natural products have received relatively li

Total Synthesis of Anti-Cancer Meroterpenoids Dysideanone B and Dysiherbol A and Structural Reassignment of Dysiherbol A

The first total synthesis of marine anti-cancer meroterpenoids dysideanone B and dysiherbol A have been accomplished in a divergent way. The synthetic route features: 1) a site and stereoselective α-position alkylation of a Wieland–Miescher ketone derivative with a bulky benzyl bromide to join the terpene and aromatic moieties together and set the stage for subsequent cyclization reactions; 2) an intramolecular radical cyclization to construct the 6/6/6/6-tetracycle of dysideanone B and an intramolecular Heck reaction to forge the 6/6/5/6-fused core structure of dysiherbol A. A late-stage introduction of the ethoxy group in dysideanone B reveals that this group might come from the solvent ethanol. The structure of dysiherbol A has been revised based on our chemical total synthesis.

Total Synthesis of Kadcoccinic Acid A Trimethyl Ester

The first total synthesis of the trimethyl ester of kadcoccinic acid A is described. The central structural element of our synthesis is a cyclopentenone motif that allows the assembly of the natural product skeleton. A gold(I)-catalyzed cyclization of an enynyl acetate led to efficient construction of the cyclopentenone scaffold. In this step, optimization studies revealed that the stereochemistry of the enynyl acetate dictates regioisomeric cyclopentenone formation. The synthesis further highlights an efficient copper-mediated conjugate addition, merged with a gold(I)-catalyzed Conia-ene reaction to connect the two fragments, thereby forging the D-ring of the natural product. The synthetic strategy reported herein can provide a general platform to access the skeleton of other members of this family of natural products.

Studies towards the Total Synthesis of Kadcotrione B

A convergent and efficient approach towards the total synthesis of Kadcotrione B is described. For this purpose, the syntheses of two fragments, 6/6/5-fused tricyclic ring and C-9 side chain, were accomplished. The salient features of these syntheses are

Total Synthesis of Paspaline A and Emindole PB Enabled by Computational Augmentation of a Transform-Guided Retrosynthetic Strategy

We report the total syntheses of two indole diterpenoid natural products, paspaline A and emindole PB. Paspaline A is synthesized in a 9-step sequence from commercially available materials. The first total synthesis of emindole PB is accomplished in 13 steps and confirms a previously ambiguous structural assignment. Density functional theory calculations are utilized to interrogate the key carbocationic rearrangement in a predictive capacity to aid in the selection of the most favorable precursor substrate. This work highlights how retrosynthetic design can be augmented with quantum chemical calculations to reveal energetically feasible synthetic disconnections, minimizing time-consuming and expensive empirical evaluation.

TETRAHYDRONAPHTHALENE DERIVATIVES USEFUL AS NRF2 ACTIVATORS

Provided are compounds of Formula I, or pharmaceutically acceptable salts thereof, and methods for their use as Nrf2 activators and for their production.

PYRIMIDINE TRICYCLIC ENONE DERIVATIVES FOR INHIBITION OF RORγ AND OTHER USES

Disclosed herein are compounds of the formulas: as well as analogs thereof, wherein the variables are defined herein. Also provided are pharmaceutical compositions thereof. In some aspects, the compounds and compositions provided herein may be used to inhibit RORγ and/or reduce the expression of IL-17. Also provided are methods of administering compounds and composition provided herein to a patient in need thereof, for example, for the treatment or prevention of diseases or disorders associated with inflammation or autoimmune disorders.

Pinacol Coupling Strategy for the Construction of the Bicyclo[6.4.1]tridecane Framework of Schiglautone A

The synthesis of the tricyclic carbon framework of schiglautone A (1) is reported herein. The generation of the bicyclo[6.4.1]tridecane 19 was accomplished via a SmI2-mediated pinacol coupling of dialdehyde 18. The side chain in 18 was introduc

Gaining Synthetic Appreciation for the Gedunin ABC Ring System

Gedunin, first isolated in 1960, displays a remarkable range of biological activity, but has yet to receive dedicated synthetic attention from a ground up construction perspective. Presented herein is a successfully executed approach to the fully function